Hello and welcome to my guide on GTA Online Story Progression.
If you are new to GTA Online, and find yourself confused with where to begin, or if you are a veteran, who figured it would be fun to try and play the game in a story-driven way, this guide could be for you.
One thing I want to get out of the way first though. This is NOT A MONEY-MAKING GUIDE! In fact, following this progression will ultimately mean that you could lose out on passive income for longer than if you focused on doing the most profitable things first. If you're hoping for progression on the fastest ways to set up passive income or money-grinding businesses, there are plenty of those here, and on Youtube. You can always still come back here at a later time, should the need for a narrative string ever strike your fancy.

If the length of the guide puts you off, you can go to the TL;DR section near the bottom, where only the missions and mission series names are listed in order.

So without further ado, let's begin!

In the previous versions of GTA V Online, you were fresh off the plane, and ready to experience Los Santos and San Andreas for the first time.
However, the Enhanced Edition has changed this up, replacing it with the Career Builder.
This new system puts you as an established resident of the area, and will have you starting as a business owner.
The most important thing here is to pick whatever suits your own character fantasy best, to make the best overarching narrative in your own head. I do have a couple points if you’re unsure what to do.
From a narrative standpoint, and to more closely follow the guide, the Executive option, which is tied to the Office, would be the optimal start, as this would narratively be the first business you’d buy into.
However, given that you are being somewhat forced to pick a “career path” that will put you ahead of the earliest story beats regardless of what you choose, another good option would be the Nightclub Owner (narratively the last of the 4), due to how the Passive income you get from the Nightclub safe after setting up the business is insanely good if you remember to drop by occasionally to throw out problematic guests.
These are the best pointers I can give. Of course, if your own headcanon sees you starting as a Biker, making his way up the ladder in the criminal underworld of Los Santos, then naturally the Biker start will be right for you, regardless of when in the timeline it was originally released.
Note that if you already had a character in the Legacy version, and port them over, you will not be confronted with this Career Builder, and will continue where that character left off.

The first thing to do after the tutorial is Contact Missions. These become available at rank (level) 5. If you are not rank 5 after the Tutorial, Fortunately, at this stage of the game, there are plenty of activities now to get you to that level. You can hold up the stores around the map... maybe drive a taxi or deliver pizzas. Or if you have 500+ dollars in-game, you can spin the wheel at the Diamond Casino and Resort daily, which is likely to give you a huge RP boost to increase your rank.

All Contact Missions have a Rank they become available at. However, if you have a friend who is the appropriate rank, they can invite you to a lobby for that mission, without you having to meet the requirement yourself. Some of the missions are also Co-op only. I will mark this in brackets if so.

All Contact Missions come in 3 difficulties, Easy, Normal, Hard. Whichever you pick doesn't matter, the mission will be the same. It only really determines how much money you get in the end, and how tough the enemies are and how much damage you take. Though if you're new, I don't recommend Hard mode right off the bat.

The Contact Missions generally are VERY LOOSELY story related. But some do trigger cutscenes, and there does exist a thread between them. But if you don't have anyone to co-op with, or just aren't high enough level for the next one, that's OK, you can come back to them later without it breaking immersion. No reason to halt your progress to find people to play with or grind rank until the next mission is available. That might just burn you out on the idea.

So how do you access Contact Missions? There are two ways, but the recommended way is to open your menu (esc on keyboard), and finding the missions tab.
From there, you can select all Contact (or Contact adjacent) missions you have access to, and start a lobby from there.
The other method is to go into your action menu (M on keyboard), and selecting to see Mission Blips. This is going to light up your minimap like a Christmas tree with more cluttered Blips than a Ubisoft Open-World game, so doing this is not recommended (except for Freemode Missions, which will have their own section.)

Here I will list the order to do the missions in. I'll tell you the necessary rank to access it, who you're doing the mission for, and if it cannot be done solo, I will add how many minimum players are needed.

Ballas to the Wall - Lamar Davis - Rank 5
Where Credit's Due - Simeon Yetarin - Rank 5
Rockford Roll - Simeon Yetarin - Rank 5
Rich Men in Richman - Simeon Yetarin - Rank 5
Chasers - Simeon Yetarin - Rank 5
It Takes a Thief - Simeon Yetarin - Rank 5
Pier Pressure - Gerald - Rank 6
Death Metal - Gerald - Rank 6
Deal Breaker - Gerald - Rank 6
Flood in the LS River - Gerald - Rank 6
Meth'd Up - Gerald - Rank 7
No Hay Bronca - Gerald - Rank 8
Gentry Does It - Simeon Yetarin - Rank 10
All in the Game - Simeon Yetarin - Rank 10
El Burro Heists - Simeon Yetarin - Rank 10
Blow Up - Simeon Yetarin - Rank 12
Gassed Up - Gerald - Rank 12
(After this, you should trigger TP Industries, a cutscene map blip at Trevor's trailer in Sandy Shores, which leads into working for him and Ron)
Romance Isn't Dead - Ron Jakowski - Rank 13
Violent Duct - Gerald - Rank 15
Chasers II - Simeon Yetarin - Rank 16
San Andreas Seoul - Lamar Davis - Rank 16
Ticket to Elysium - Lamar Davis - Rank 18
Cops Capacity - Lester Crest - Rank 19
Blow Up II - Simeon Yetarin - Rank 20
Going Down the GoH - Lamar Davis - Rank 20
Caught Napping - Lamar Davis - Rank 20
Fueling the Flames - Ron Jakowski - Rank 20
Lost My Mind - Trevor Philips - Rank 20
Out of Court Settlement - Martin Madrazo - Rank 22
Landing Strip - Lester Crest - Rank 22 (Co-op min. 2 players)
Death From Above - Martin Madrazo - Rank 24
A Titan of a Job - Lester Crest - Rank 24
Lost MC RIP - Lamar Davis - Rank 25
Turbine Carbine - Ron Jakowski - Rank 25
Daemon run - Ron Jakowski - Rank 25 (Co-op min. 2 players)
Last Chopper Outta LS - Lester Crest - Rank 25 (Co-op 2 players)
High Priority Case - Lester Crest - Rank 25 (Requires Helicopter, or access to call Merryweather helicopter services which becomes available at rank 30)
Base Invader - Ron Jakowski - Rank 27
Crystal Clear Out - Trevor Philips - Rank 28
War and Pieces - Gerald - Rank 30
No Smoking - Lamar Davis - Rank 30
Crank Up the Volume - Ron Jakowski - Rank 30
Quarry Quarry - Lester Crest - Rank 30
By Land, Sea and Air - Lester Crest - Rank 30 (Co-op min. 2 players)
Blow Up III - Simeon Yetarian - Rank 31
Chumash and Grab - Gerald - Rank 35 (Co-op min. 2 players)
Check Out Time - Martin Madrazo - Rank 35
(Freemode Co-op missions could be started from here on out - see next section)
Teaser Trailer - Lester Crest - Rank 40
Water The Vineyard - Martin Madrazo - Rank 40
Grab Your Ballas - Martin Madrazo - Rank 40
Stick Up the Stickup Crew - Martin Madrazo - Rank 40
The Los Santos Connection - Martin Madrazo - Rank 40
Dish the Dirt - Gerald - Rank 45
Four Trailers - Lester Crest - Rank 45
Editor and Thief - Martin Madrazo - Rank 45
Mixed up with coke - Martin Madrazo - Rank 45
Dry Docking - Martin Madrazo - Rank 45
Cleaning the Cat House - Martin Madrazo - Rank 45
Out of Harmony - Trevor Philips - Rank 50
Extradition - Martin Madrazo - Rank 50
Holed Up - Burton - Martin Madrazo - Rank 50
Show Me the Monet - Martin Madrazo - Rank 55
Landing Gear - Ron Jakowski - Rank 55 (Co-op min. 4 players)
Wet Workers - Ron Jakowski - Rank 55
Bust Out - Lester Crest - Rank 55
Sinking Feeling - Lester Crest - Rank 55 (Co-op min. 2 players)
The Parking Garage - Lester Crest - Rank 55 (Co-op min. 2 players)
Hack and Dash - Lester Crest - Rank 60
Satellite Communications - Trevor Philips - Rank 60
Method in the Madness - Trevor Philips - Rank 65 (Co-op min. 2 players)
On Maneuvers - Lester Crest - Rank 65
Judging the Jury - Martin Madrazo - Rank 65 (requires careful planning or fast vehicle to do solo)
Defender - Martin Madrazo - Rank 70
Docks to Stock - Lester Crest - Rank 70 (Co-op min. 2 players)
Stocks and Scares - Lester Crest - Rank 70
Chopper Tail - Trevor Philips - Rank 70
Diamonds are for Tervor - Trevor Philips - Rank 70
Rooftop Rumble - Martin Madrazo - Rank 75
Trash Talk - Martin Madrazo - Rank 81

There are some additional Contact missions which are somewhat hidden and hard to come by. They are only available from the map blips, and only at specific times of day.
They generally have lower rank requirements than the other missions, but based on their names and what they are about, clearly takes place after some of the other, higher ranked contact missions. In the Contact Missions list, I have in brackets specified when it would make sense to start them. From that point on, feel free to go do them at any point that fits in. You are also free to finish all of the Contact missions before doing these.
Since these are so out of the way, and there are no real cutscenes or consequences related to them you can also feel free to skip these if you prefer.
To access them, you will have to enable the blips in the action menu, like explained in the Contact Mission section. You will then have to drive to the blip to start the mission. From my experience, as long as you have successfully started a lobby, you will not be booted out of the mission lobby if the in-game time exceeds the availability of the mission blip.

I will list these in the same way as the Contact Missions, but with the added availability time, as well as the approximate location of the blip on the map.

Crystal Clear Out II - Trevor Philips - Rank 16 - Availability: 15:00 - 23:00 - Senora Desert, Blaine County
Factory Closure - Martin Madrazo - Rank 18 (Co-op min. 3 players) - Availability: 07:00 - 17:00 - La Mesa
Dirt Road - Trevor Philips - Rank 19 - Availability: 14:00 - 22:00 - North Chumash
Coasting - Martin Madrazo - Rank 25 - Availability: 20:00 - 06:00 - Palomino Highlands
Potshot - Trevor Philips - Rank 25 - Availability: 04:00 - 12:00 - Braddock Farm
Close Action - Trevor Philips - Rank 35 (Co-op, exactly 4 players) - Availability: 12:00 - 20:00 - Senora Desert
Coveted - Martin Madrazo - Rank 36 - Availability: 00:00 - 08:00 - RON Alternates Wind Farm
Crystal Clear Out III - Trevor Philips - Rank 40 - Availability: 07:00 - 15:00 - Blaine County

Locations can be difficult to track down. Recommend finding Youtube videos for footage of the specific locations.
If possible, I will update the guide with links to that at a later time.

The High Life, Independence day, and Flight School updates added a couple additional Contact Missions. These are available at lower ranks, but are canonically taking place after the original Contact Missions list. However, their storyline placement is not very important, so if you are struggling to have the necessary rank for the original ones, feel free to add these in the mix if you have already started the first original mission for each of the contacts.

GTA Today (High Life) - Simeon Yetarian - Rank 12 (Co-op min. 2 players)
Hit 'Em Up (High Life) - Gerald - Rank 14
Denial of Service (High Life) - Lester Crest - Rank 14
Master Data (High Life) - Lester Crest - Rank 16
On the List (High Life) - Martin Madrazo - Rank 18
Artificial Scarcity (High Life) - Martin Madrazo - Rank 19
Handle with Care (High Life) - Martin Madrazo - Rank 20
Crime Scenester (High Life) - Lester Crest - Rank 20
Hard Labor (Independence day) - Gerald - Rank 19
Time To Get Away (Independence Day) - Martin Madrazo - Rank 21
Chop Chop (Flight School) - Trevor Philips - Rank 43 (Co-op min. 2 players)
Effin' Lazers (Flight School) - Martin Madrazo - Rank 44 (Co-op min. 2 players)

Finally, we reach the point where some real story progression can be felt. Now that we have established ourselves as competent crooks, Heists will become available. This requires you to own any High-End apartment. It doesn't matter if it's a normal High-end Apartment, a fancy interior one, or even a Stilt House (which is still considered an apartment). All have a Heist room.
As long as you are the host, you will be forced to do these in order. You will also have to wait about 48 minutes between each heist. before Lester will call you about the next one.

The heists consist of setup missions, and the heist itself. If possible, it's recommended to do these with the same people all the way through for extra bonuses, but is not necessary.

The Heists in order are:
The Fleeca Job (2 players)
The Prison Break (4 players)
The Humane Labs Raid (4 players)
Series A Funding (4 players)
The Pacific Standard (4 Players).

To save on down-time between heists (and while you already have a group together), you can begin to complete the next Mission series, Lowriders, as well. (seen next section)
While it takes place canonically after the heists, there are no real references to the events of the heists in that series of missions, so it should stay story-consistent. But you can also wait until after you're done to progress as normal.

Lamar is at it again in the Lowriders series, which introduces Benny's Original Motor Works, an additional vehicle modification shop.

The missions can be accessed from Lamar's "L" Blip on the map (there might be 2 of these on the map, the other just triggers a phone call prompting you to buy something... go to the other one if that happens)

The missions have an exact player count to start, and are as follows:

Community Outreach (4 players)
Slow and Low (2 Players)
It's a G Thing (2 Players)
Funeral Party (4 players)
Lowrider Envy (2 Players)
Point and Shoot (2 Players)
Desperate Times Call For... (4 players)
Peach Offerings (4 players)

There will be a short delay between each mission, where you wait for Lamar to call you about the progress.

These missions will automatically be done in order if you are the host, by visiting the L blips on the map.
Once all are done, they can be replayed from the missions menu like the Contact Missions.

Finally, we get to businesses.
An Executive Office can be purchased from Dynasty 8 Executive now. This will let you become a CEO of your own company, to use as a front for your Criminal activities. With it, you will get access to new ways to make money. You can buy warehouses, and go on short missions to acquire the cargo. Do this if you like. None of them are story related. You can also occasionally do an export for bonus cash by talking to your assistant. There is an additional feature in the office, the Import/Export Garage, and Special Exports Missions, but we will get back to those, as those technically were released a bit later, so I will give them their own section.

Next, we will talk about the MC Clubhouses. These allow you to run your own Motorcycle Club, and functions in a similar way to the Office for the most part. You buy one at Maze Bank Foreclosures. You can restock your bar with booze for some extra cash flow.
You can buy additional business ventures from your Clubhouse Computer, to set up shops to print counterfeit cash, forge documents, and different illegal substance production facilities..
MC Clubhouses however, come with an actual mission board, which would be relevant to go over, so we will cover that in this next section, and then return to the Executive Office Import/Export missions.

Three Clubhouse contracts will be available at your Clubhouse Noticeboard. Clearing all 3 will spawn new ones. Otherwise, you can change session, which should also spawn new ones.
There is no "order" to do these in, so I will list them in alphabetical order. Though 2 of them were added later, so those 2 will be at the bottom, if you prefer to do those last.

By the Pound
Cracked
Fragile Goods (Co-op min. 2 players)
Guns for Hire (Co-op min. 2 players)
Gunrunning
Jailbreak
Nine Tenths of the Law (Co-op min. 2 players)
Outrider (Co-op min. 2 players)
P.O.W.
Torched
Weapon of Choice (Co-op min. 2 players)

New Additions:
Hit the Roof
Life and Deathbikes

To get started with this, you have to buy a Vehicle Warehouse.
From there you can trigger missions to steal cars, and bring them back to the Warehouse, to sell them later. You will have to do some of these missions, in order to trigger the "Real" Missions, called "Special Vehicle Work". You will only have to successfully steal the cars, selling them again is not required to unlock the missions. So you only do that for your own profit. A total of 32 Vehicles will have to be stolen to unlock all missions.
Keep in mind that ALL of the Special Vehicle Works Missions require at least 2 players, so I will not list this on every mission here.
The missions, and conditions to unlock the Special Vehicle Work Missions, are as follows:

Escape Escort (After 4 Vehicles)
Breakdown Recovery (After 8 Vehicles)
Cleanup Op (After 12 Vehicles)
Asset Seizure (After 16 Vehicles)
Firewall Protection (After 20 Vehicles)
Coast Guard Duty (After 24 Vehicles)
End of Transmission (After 28 Vehicles)
Arms Embargo (After 32 Vehicles)

Once you have either an Executive Office, or a MC Clubhouse, and can be either a CEO or MC President, you can buy a Bunker from Maze Bank Foreclosures, for Gunrunning. This business allows you to produce and sell weapons, or conduct research to unlock gun and weaponized vehicle upgrades. You will also be able to sell weapons to Ammu-nation (this can be done regardless of you having stock or not, as a recurring thing).
Like with the Office, there are resupply missions. While the missions themselves are not relevant for story, you will need to do at least 14 of them to unlock access to Mobile Operations missions, similarly to how you unlocked Special Vehicle work missions.
Once the Bunker is owned, you can buy a Mobile Operation Center from Warstock. This can be customised, but the standard version will always still come with the command centre you can start the Mobile Operations missions from. You can spawn this vehicle outdoors and enter it, so you are not locked from starting them in 1 place. Like the Special Vehicle Work missions, these all require 2 players minimum to start.

The missions are:
Severe Weather Patterns (Complete 2 Resupply missions)
Half-Track Bully (Complete 4 Resupply missions)
Exit Strategy (Complete 6 Resupply missions)
Offshore Assets (Complete 8 Resupply missions)
Cover Blown (Complete 10 Resupply missions)
Mole Hunt (Complete 12 Resupply missions)
Data Breach (Complete 14 Resupply missions)
Work Dispute (Complete Data Breach)

Next is the Hangar.
Not much here in terms of missions really. You have restock missions you do to get stock, and then you sell the stock. All obviously heavily reliant on flying vehicles.
You will of course also be able to store flying Vehicles here, instead of using the Pegasus phone services to spawn them.
I suggest you buy a Hangar in the Military base, as it grants you limited access to the base, which comes in mighty handy, especially if you plan on getting all collectables at some point. The Airport is already freely available to everyone at this stage of the game, so buying one there doesn't give you any extra perks.

Now we get back to something that really feels like progression, which is more heisting.
The Doomsday Heist requires 2 players (but you can be up to 4 if you wish). To access it, you buy a Facility from Maze Bank Foreclosure.
The Heist is divided into 3 parts:
The Data Breaches
The Bogdan Problem
The Doomsday Scenario.
Each of these have both Preparation missions and Setup Missions.
Once again, like with the Original Heists, the first time around while you yourself host, you are locked into doing these in order, so no need to worry about doing any missions here out of chronological order.
Once all completed, you can start up whichever of the 3 you'd like, you don't have to go through all 3 in order again.

Back to Contact Missions. A new series was added. These originally required at least 2 players, but this has been lowered to be soloable now.
The Missions are easy to distinguish in order:
Dispatch I
Dispatch II
Dispatch III
Dispatch IV
Dispatch V
Dispatch VI
Keep in mind, you should start these from the missions menu like any other Contact Mission. Going to the Blip on the map at Madrazo's place will start up a random mission out of the assortment. There are no cutscenes for this, so no reason to go to the map location.

Next, it's time to acquire a Nightclub. This again is done from Maze bank Foreclosure.
The Nightclub is a great passive business, generating income just by playing, as long as you keep the club advertised and the guests happy. This was made a lot easier with the possible spawn of angry guests to throw out of your club. But you can also always do the promotion missions.
The Nightclub starts out needing supplies, so you have a "setup" mission of sorts, which won't be replayable.
Once your Nightclub is running, you also gain extra passive crates of goods to sell in your basement warehouse(s). You can do sell missions for those when you have enough.
In Warstock, you can buy the Terrorbyte to store in your clubhouse. This gives you access to Client Jobs. These jobs are more "randomised" than the ones from the Mobile Operation Center, but I'd still suggest doing them all once each.
The jobs are:
Robbery in Progress
Data Sweep
Targeted data (requires Drone station purchased)
Diamond Shopping (requires Drone station purchased)
Collector's Pieces (Co-op min. 2 players)
Deal Breaker (Co-op min. 2 players)

Simeon Yetarian is at it again, and is offering new Contact Missions. As with the Dispatch missions from Madrazo, do not use the map blip to start these, or you will just get a random one.
The missions are:
Repo - Blow Up IV
Repo - Sasquashed
Repo - Under the Hammer
Repo - Do You even Lift?
Repo - GTA Today II
Repo - RV Nearly There?
Repo - Burn Rate
Repo - Simeonomics

Now we get to a bit of a pricey one.
You will need to buy the Penthouse at the Diamond Casino and Resort. You can buy the absolute bare minimum, and always just buy upgrades later if you feel like using it as a home.
Owning this gives you access to the Casino Story Missions. These are again automatically played in order. These also used to require 2 players, but can now be done solo. The Missions are:
Casino - Loose Cheng
Casino - House Keeping
Casino - Strong Arm Tactics
Casino - Play to Win
Casino - Bad Beat
Casino - Cashing Out
Once completed, they can be replayed from the contact Mission Menu.

This is not all however. After you finish this, You will receive a car as a reward. Agatha Baker will also start calling you on a daily basis, asking you to do Casino Work. You can also call her yourself for more work, but it's on a timer since you last did a job. The Job will be randomly selected from the list, so might take a while to get all of them.
Casino work has no bearing on the story... However, there is 1 important note to keep in mind. There are 3 secret missions. One of the missions will only trigger when Agatha calls you, if you have diligently been taking her calls. Should you refuse her call, or not take the mission when prompted, this will make her stop calling, and set your progress towards getting this Secret Mission back to 0. (Honestly though, it's really not worth the hassle of having to deal with her calling you near the start of every new daily session of the game, so up to you if you'll ignore it or not).

The Missions are:
Bargaining Chips
Best Laid Plans
Department of Defense
Fake News
High Rollin'
Judgement Call
Lost in Transit
One Armed Bandits
Recovery Time
Safe Bet
Severance
Undisclosed Cargo
When the Chips are Down

Secret Missions:
Damage Control (Can trigger at random after you take a MacBeth Whisky shot at the Casino Bar or your own Penthouse Bar. Can take A LOT of attempts. If you keep being put in the Bathroom, leave the Casino, and go back in before you try again.)
Under the Influence (Triggers if you request a job while drunk (or leave the casino drunk before your daily Agatha call). Drink anything other than MacBeth Whisky Shots, as those make you black out, and cannot trigger this)
Tour de Force (All non secret Casino Missions must have been completed. 10 Real Life Hours must have passed since your last mission. You must actively be a CEO or MC President. You must enter the Casino or Penthouse. If you never refused work from Agatha when she called you, there is a chance she will call you while you're inside, to give you this mission).

After doing the Casino Story Missions... why not rob the place?
Buy an Arcade from Maze Bank Foreclosure as a front, and plan your heist. This mission takes place AFTER the story of GTA V, unlike most of the other missions before this, which took place before or simultaneously. Lester Comes out of Retirement to help you prepare the heist.
This Heist can be done in 3 ways, and has multiple approaches. Definitely recommended to come back to later. But for the "Story progression" part, you will only need to complete the heist once, in whichever of the 3 approaches you prefer. Do keep in mind though, that whichever approach you pick will be unavailable next time you want to do the heist.
The approaches are:
Silent and Sneaky
The Big Con
Aggressive
No reason to go into details about the heist and approaches further here, as you cannot mess up the story progression bit. If you want more details about the heist itself, there are plenty of other guides around, and on Youtube.
The Arcade is also a business, and will generate you some passive income, based on how many arcade machines you have. You can also play the Arcade machines you own, to play minigames.

More Contact Missions, in style of Dispatch and Repo work, is Gerald's Last play.
The Missions are:
Bad Companies
Deal With It
End Product
Fast Peddling
Go Figure
Make Ends Meat
Again, do these through the missions menu, as using the blip on the map gives you a random mission.

Next up, you're going to use all of that money you hopefully saved up to buy a Superyacht.
These are very expensive, the cheapest, non-upgraded one costing you 8 million dollars.
Suffice it to say, you're not making your money back from these missions.

Regardless, the missions are:
Overboard
Salvage
All Hands
Icebreaker
Bon Voyage
D-Day

And hey... now you have a yacht you can live in... gotta spend that money on SOMETHING after all!

Most notorious for being the first heist you could do solo, being the most profitable heist, and being the most repeatedly nerfed money making method in the game, comes the Cayo Perico Heist.
You need to go to the music locker under the Diamond casino and resort to get started. You will need to buy the Kosatka Submarine from Warstock in order to plan the heist.
As part of the story, you will also visit the island for recon, which will prompt English Dave to give you his car free of charge.

Next you can go to the LS Car Meet. There you will meet some new faces, and get the option to buy an Auto Shop. After an initial mission, you will have a mission board with the Robbery Contracts. You will have 3 available at a time, and they will rotate into new ones. If you currently have one of them active, it will stay active until you finish it, or decide to cancel it.
These Six Missions were originally available:
The Bank Contract
The Data Contract
The Superdollar Deal
The Prison Contract
The Agency Deal
The E.C.U Job

The following 2 were added a little later:
The Lost Contract
The Union Depository Contract.

NPCs will also bring their cars to your Auto Shop, which you can tune for them to their specifications, and deliver for extra cash. These are Generic missions though, and not relevant for story progression.

Next up as a big content update.
You will be able to buy an Agency, in which you will partner with Franklin from GTA V's story mode to run a business.
You will be able to do Security Contracts, which are semi-generic missions. The more you do, the more passive money your safe will generate, up to a cap.
The missions are:
Recover Valuables
Vehicle Recovery
Gang Termination
Rescue Operation
Asset Protection
Liquidize Assets.

Franklin will also offer Payphone hit missions. These are started when a blue payphone icon appears on the map, and you can hear a phone ringing. He will give you a short rundown of your mission over the phone, and you will get a text with a preference in execution which nets you more money if successfully followed. You can't force which type of mission you get, but if you wish to do all of them and keep track, they are as follows:

The CEO
The Cofounder
The Judge
The Popstar
The Tech Entrepreneur
The Trolls
The Dealers
The Hitmen

Most importantly though, is the namesake, The Contract.
The two of you will get in touch with a bigshot client for a big payday. You will get a little bit of freedom to pick which order you want to do some of the missions in, but they must all be completed for the finale, so there isn't a need to list them here. Go with whatever order you feel like.

Once The Contract has been successfully completed, you will also get access to some Co-op Missions (2 player locked), called Short Trips. You and a pal go get high with Franklin and Lamar, and end up controlling them over a series of 3 missions. These again are linear, and forced on you the first time so I won't list the order. You can redo them from the Mission menu like Contact missions.

After a delay, you will also be able to redo (most of) The Contract again from the Agency computer.

Operation Paper Trail is next. These are more contact missions, but unlike the Dispatch, Repo and Last Play ones, this one is fully voiced, and has an actual forced story progression. To start this, you will go to the big U blip on the map. Once done, they can be replayed in any order from the Mission menu.

Next up, in similar style to Operation Paper Trail, we have the First Dose Missions, which are started by going to the R in Sandy Shores. After the first mission, this will change to a D, and the location changes. In addition, these missions also have cutscenes.
All the missions are done by going to the blip, and will be done in order
There are 6 First Dose Missions:
Welcome to the Troupe
Designated Driver
Fatal Incursion
Uncontrolled Substance
Make War not Love
Off the Rails.

Once done, the Acid lab will be available to you.

The missions continue with the second half, called Last Dose. These are started the same way, by going to the D map blip, and culminated in getting a new Free car.
The Last Dose Missions are:
This is an Intervention
Unusual Suspects
Friedmind
Checking In
BDKD

After the First dose missions, you are also able to call Dax and get a random "Fooligan Job".
These are semi-generic jobs again, and the following 5 variants exist:
Crop Dustin'
Heavy Metal
Liquid Assets
Working Remotely
Write-off

San Andreas Mercenaries is another mission line, which was added to be available from the Avenger vehicle, which can be stored in either a Facility or a Hangar. You will need to buy the Operation Terminal in the Avenger to access the missions.
The Primary Mission line is Project Overthrow, which consists of 6 missions:
Reporting for Duty
Falling In
On Parade
Breaking Ranks
Unconventional Warfare
Shock & Awe

Besides that, there are the Semi-generic LSA Operations, of which there are 3 types.
Direct Action
Surgical Strike
Whistleblower

Next we have the Chop Shop update, where you can buy a Chop shop from Maze Bank Foreclosure.
This will let you get a tow truck and salvage vehicle parts. But of course, like most other businesses, this is only a front for your Salvage Yard Robberies.
There are 5 Salvage Yard Robberies. 3 will be available, and rotate out once a week (on Thursdays, unless there's a major patch, in which case it's on Tuesdays).
You will get to select which of the 3 cars you want to go for, and then you will start preparing for the robbery type assigned to it.
The different types of missions are:
The Duggan Robbery
The Gangbanger Robbery
The Cargo Ship Robbery
The Podium Robbery
The McTony Robbery

Once acquired, you will be asked if you want to sell it to Yusuf Amir, or salvage it.
Unless your driving skills at this point are still somehow atrocious, you should always sell the vehicle, as that will give you more money. But you will need to drive it to the docks, and any damage will reduce the value of the car.
Occasionally, a car from a robbery will be claimable. This is denoted by a purple outline and a Garage symbol. You will need to pay a small fee to do so, but it's always worth doing, as even if you'd never use the car, you can sell it at a Los Santos Customs for more money than if you had sold it to Yusuf Amir anyway. If you own a document forgery, this cost will be halved.

By going to the V at the police station in Vespucci, you can start the Cluckin' Bell Farm Raid from Vincent. If you were following the guide, you will already know this guy as a former employee from the Diamond Casino, who was fired.
This is essentially a heist, but it plays a bit differently. You go to the V blip for each progression of the heist, and will do so again if you ever want to retry it.
The missions are:
Slush Fund
Breaking and Entering
Concealed Weapons*
Hit and Run*
Disorganized Crime
Scene of the Crime

The two marked with * can be done in either order. Also, if you mess up during Disorganized Crime, the finale will be in a loud variation. They are treated as 2 different approaches, but in reality, aren't very different from each other.

Bottom Dollar Bounties lets you run your own Bail enforcement office.
After buying one, you will be able to take on bounties.
You will have one "Most Wanted" target per day, which are all unique missions, of which there are Six in total:
Grance
Lieberman
O'Neil
Thompson
Song
Garcia
The order you do these in does not matter, so simply start with whoever is available to you on that day, and keep track from there.
You will also have 3 other bounties available which rotates about every 48 minutes.
These are more Semi-Generic, and 3 targets will have the same mission style
Bank Robbery: Ricky Ji, Tommy Lim, LJ Ha
Prison Bus: Cook Kenzie, Marquel Green, Colby Wright
CCTV: Lil Prince, Xavier Fremond, Jalen Kennedy
Clubhouse: Serenity Pierce, Angel Kenny, Rylee Rose
Mansion Intimidation: Sabrina Gray, India Wood, Brigitte Foster
Arcade: Beau Duggan, Bill Duggan, Hunter Duggan

I would recommend doing at least one of each mission type, but feel free to "Catch 'em all" so to speak.

The Bottom Dollar Bounties update also came with the option to do Dispatch Work. To start those, you will need to own a cop car. Vincent will contact you while driving to let you know how to start the missions, and will give you a random one from an assortment of 4. You cannot start these if you are currently a CEO or MC President.
The mission types are:
Office Monitored
Possession for Sale
Civil Disturbance
Malicious Mischief
With the Agents of Sabotage DLC, two more mission types were added:
Health Code Violations
Obstruction of Justice

The Agents of Sabotage DLC added the FIB Files mission line, with the option to buy the Darnell Bros. Garment Factory.
There are 4 missions, with 1 being a priority mission for the week that will pay double money for completing it once that week.
You can also start up these missions from an in-game phone app once the Garment Factory is purchased and visited.
The missions are as follows:
The Brute Force File
The Black Box File
The Fine Art File
The Project Breakaway File

By buying the McKenzie Field Hangar, two new mission lines become available.
The main one is Oscar Guzman Flies Again, which presents you a storyline to complete in order.
The missions are:
Up and Running
Setup: Mogul
Setup: Intel
Setup: Iron Mule
Setup: Ammunition
The Titan Job.
The mission chain is designed as a sort of heist in a similar style to the Cluckin' Bell Farm Raid, but with an extra emphasis on flying.

Once Up and Running is complete, you also have access to the Arms Trafficking missions.
There are 4 missions picked at random when you pick it from the computer in the Hangar, or call Oscar Guzman on the phone. These are not tied to a storyline, and function more as bonus randomized missions to do for the business to make money,
The missions are:
Destroy the rival shipments
Steal the Weapons
Deliver the weapons
Steal the Duster 300-H

The Money Fronts DLC allows you to buy the Hands on Car Wash, and once purchased, also allows you to buy Higgins Helitours and Smoke on the Water.

Each of these have Money Laundering work, which are sets of 4 types of missions for each business, as well as 1 Legal work activity you use to reset the heat, as you cannot do the jobs with maxed out heat.

The missions are randomized, but if you want to try each, they are as follows:

Hands On Car Wash:
Recover the Cash (Stockade)
Recover the Cash (Stash Car)
Steal the Rival's Cash
Torch the Rival Operation

Higgins Helitours:
Recover the cargo
Recover the helicopter
Deliver the cargo
Recover the cash case

Smoke on the Water:
Torch the weed farms
Collect the fertilizer
Recover the product
Eliminate the rival dealers

Buying the Car wash also gives you access to Mr. Faber Work. There are 6 missions here, and can be accessed from either of the 3 businesses, though they are not unique to the business you start it from.
The missions are:
Liquid Market
ROI
Compound Interest
Mutual Funds
Current Liabilities
The Monopoly

They seem to be given in the above order, and then loop through again once all are done.

Here Is a quick list to summaries, or if you just want the names of the missions and don't care for details:

Contact Missions:
Ballas to the Wall - Lamar Davis - Rank 5
Where Credit's Due - Simeon Yetarin - Rank 5
Rockford Roll - Simeon Yetarin - Rank 5
Rich Men in Richman - Simeon Yetarin - Rank 5
Chasers - Simeon Yetarin - Rank 5
It Takes a Thief - Simeon Yetarin - Rank 5
Pier Pressure - Gerald - Rank 6
Death Metal - Gerald - Rank 6
Deal Breaker - Gerald - Rank 6
Flood in the LS River - Gerald - Rank 6
Meth'd Up - Gerald - Rank 7
No Hay Bronca - Gerald - Rank 8
Gentry Does It - Simeon Yetarin - Rank 10
All in the Game - Simeon Yetarin - Rank 10
El Burro Heists - Simeon Yetarin - Rank 10
Blow Up - Simeon Yetarin - Rank 12
Gassed Up - Gerald - Rank 12
(After this, you should trigger TP Industries, a cutscene map blip at Trevor's trailer in Sandy Shores, which leads into working for him and Ron)
Romance Isn't Dead - Ron Jakowski - Rank 13
Violent Duct - Gerald - Rank 15
Chasers II - Simeon Yetarin - Rank 16
San Andreas Seoul - Lamar Davis - Rank 16
Ticket to Elysium - Lamar Davis - Rank 18
Cops Capacity - Lester Crest - Rank 19
Blow Up II - Simeon Yetarin - Rank 20
Going Down the GoH - Lamar Davis - Rank 20
Caught Napping - Lamar Davis - Rank 20
Fueling the Flames - Ron Jakowski - Rank 20
Lost My Mind - Trevor Philips - Rank 20
Out of Court Settlement - Martin Madrazo - Rank 22
Landing Strip - Lester Crest - Rank 22 (Co-op min. 2 players)
Death From Above - Martin Madrazo - Rank 24
A Titan of a Job - Lester Crest - Rank 24
Lost MC RIP - Lamar Davis - Rank 25
Turbine Carbine - Ron Jakowski - Rank 25
Daemon run - Ron Jakowski - Rank 25 (Co-op min. 2 players)
Last Chopper Outta LS - Lester Crest - Rank 25 (Co-op 2 players)
High Priority Case - Lester Crest - Rank 25 (Requires Helicopter, or access to call Merryweather helicopter services which becomes available at rank 30)
Base Invader - Ron Jakowski - Rank 27
Crystal Clear Out - Trevor Philips - Rank 28
War and Pieces - Gerald - Rank 30
No Smoking - Lamar Davis - Rank 30
Crank Up the Volume - Ron Jakowski - Rank 30
Quarry Quarry - Lester Crest - Rank 30
By Land, Sea and Air - Lester Crest - Rank 30 (Co-op min. 2 players)
Blow Up III - Simeon Yetarian - Rank 31
Chumash and Grab - Gerald - Rank 35 (Co-op min. 2 players)
Check Out Time - Martin Madrazo - Rank 35
(Freemode Co-op missions could be started from here on out - see next section)
Teaser Trailer - Lester Crest - Rank 40
Water The Vineyard - Martin Madrazo - Rank 40
Grab Your Ballas - Martin Madrazo - Rank 40
Stick Up the Stickup Crew - Martin Madrazo - Rank 40
The Los Santos Connection - Martin Madrazo - Rank 40
Dish the Dirt - Gerald - Rank 45
Four Trailers - Lester Crest - Rank 45
Editor and Thief - Martin Madrazo - Rank 45
Mixed up with coke - Martin Madrazo - Rank 45
Dry Docking - Martin Madrazo - Rank 45
Cleaning the Cat House - Martin Madrazo - Rank 45
Out of Harmony - Trevor Philips - Rank 50
Extradition - Martin Madrazo - Rank 50
Holed Up - Burton - Martin Madrazo - Rank 50
Show Me the Monet - Martin Madrazo - Rank 55
Landing Gear - Ron Jakowski - Rank 55 (Co-op min. 4 players)
Wet Workers - Ron Jakowski - Rank 55
Bust Out - Lester Crest - Rank 55
Sinking Feeling - Lester Crest - Rank 55 (Co-op min. 2 players)
The Parking Garage - Lester Crest - Rank 55 (Co-op min. 2 players)
Hack and Dash - Lester Crest - Rank 60
Satellite Communications - Trevor Philips - Rank 60
Method in the Madness - Trevor Philips - Rank 65 (Co-op min. 2 players)
On Maneuvers - Lester Crest - Rank 65
Judging the Jury - Martin Madrazo - Rank 65 (requires careful planning or fast vehicle to do solo)
Defender - Martin Madrazo - Rank 70
Docks to Stock - Lester Crest - Rank 70 (Co-op min. 2 players)
Stocks and Scares - Lester Crest - Rank 70
Chopper Tail - Trevor Philips - Rank 70
Diamonds are for Tervor - Trevor Philips - Rank 70
Rooftop Rumble - Martin Madrazo - Rank 75
Trash Talk - Martin Madrazo - Rank 81
--
Freemode Missions:
Crystal Clear Out II - Trevor Philips - Rank 16 - Availability: 15:00 - 23:00 - Senora Desert, Blaine County
Factory Closure - Martin Madrazo - Rank 18 (Co-op min. 3 players) - Availability: 07:00 - 17:00 - La Mesa
Dirt Road - Trevor Philips - Rank 19 - Availability: 14:00 - 22:00 - North Chumash
Coasting - Martin Madrazo - Rank 25 - Availability: 20:00 - 06:00 - Palomino Highlands
Potshot - Trevor Philips - Rank 25 - Availability: 04:00 - 12:00 - Braddock Farm
Close Action - Trevor Philips - Rank 35 (Co-op, exactly 4 players) - Availability: 12:00 - 20:00 - Senora Desert
Coveted - Martin Madrazo - Rank 36 - Availability: 00:00 - 08:00 - RON Alternates Wind Farm
Crystal Clear Out III - Trevor Philips - Rank 40 - Availability: 07:00 - 15:00 - Blaine County
--
Later Contact Mission additions:
GTA Today (High Life) - Simeon Yetarian - Rank 12 (Co-op min. 2 players)
Hit 'Em Up (High Life) - Gerald - Rank 14
Denial of Service (High Life) - Lester Crest - Rank 14
Master Data (High Life) - Lester Crest - Rank 16
On the List (High Life) - Martin Madrazo - Rank 18
Artificial Scarcity (High Life) - Martin Madrazo - Rank 19
Handle with Care (High Life) - Martin Madrazo - Rank 20
Crime Scenester (High Life) - Lester Crest - Rank 20
Hard Labor (Independence day) - Gerald - Rank 19
Time To Get Away (Independence Day) - Martin Madrazo - Rank 21
Chop Chop (Flight School) - Trevor Philips - Rank 43 (Co-op min. 2 players)
Effin' Lazers (Flight School) - Martin Madrazo - Rank 44 (Co-op min. 2 players)
--
Heists, Businesses, and Series:
Original Heists
Lowriders
MC Clubhouse Contracts
Special Vehicle Works Missions
Mobile Operations Missions
(Hangar, no real progression missions)
Doomsday Heist
Madrazo Dispatch Services
Terrorbyte Client Jobs
Premium Deluxe Repo Work
Diamond Casino and Resort Story Missions
The Diamond Casino Heist
Gerald's Last Play
A Superyacht Life
The Cayo Perico Heist
Auto shop Robbery Contracts
The Contract
Short Trips
(Payphone hits)
Operation Paper Trail
First Dose
Last Dose
San Andreas Mercenaries
Chop Shop Salvage Yard Robberies
Cluckin' Bell Farm Raid
Bottom Dollar Bounties Most Wanted Missions
Agents of Sabotage FIB Files Missions
Oscar Guzman Flies Again Missions
Money Fronts missions (Primarily Mr. Faber work)

That's all the content updates for what is currently in the game from a story standpoint.
I will of course update the guide again when more content gets released.

Of course, there is no need to follow this guide religiously. A lot of the missions are not exactly obviously referencing each other, and even some who are have some unique dialogue if you do not yet know the character in question through your own main story experience (such as the cases for Operation Paper Trail done before Doomsday heist, and working for Vincent before doing Diamond Casino).
But since it can be pretty unclear, especially to a new player, when things were added, I figured this could be a helpful tool for those like me, who like some story progression to their playthrough.

Honourable mention here goes to Arena Wars, which I have not added to the guide, due to its competitive multiplayer nature. It does have a couple cutscenes, and you can still experience those even if you simply quit out of your first match. This would go just before the Diamond Casino and Resort in the timeline, but is mostly separate from everything else.

Thank you for checking out the guide. I hope the information I compiled here has been useful to you.
Feel free to add comments, if you feel like something is missing, or you wish something was more detailed.

Have a great day!