Welcome in my first guide ever made.
At the outset I would like to apologize for overall quality this guide which might deviates from other guides you've seen. I tried my best to be short and consize instructions. I expect basic understanding of the game, so I won't explain in detail certain mechanics such as getting certificates. Before asking about the game check in game manual first.

Thanks for understanding !

Club UPDATE
Guide is outdated atm
It's missing achievements related to clubs and such due to being made within weeks of initial release. I'll try updating the guide once I start playing the game again.

...reading or looking for specific achievements I encourage you to at least take a brief look Easly Missable section first, it might safe some time and frustrations later down the line.
Achievements in that section are much harder to get and more time consuming.

Here's my reasoning behind splitting achievements to 5 categories:

• Easly Missable - Very unlikely you'll get them in your first playthrough. To obtain couple of them you have once per save chance, some can be missed due to many factors,
  
• Missable – RNG based - your at the mercy of RNG jesus,
  
• Missable – specific requirements - condtions are harder to get. You might not get them before you reach your first win,
  
• Unmissable – normal playthrough: you should get these at some point by just playing the
  game without any significant effort,
  
• Win condtions - mostly advice how to get them

Spirit of the Well: Meet the Spirit of the Well.
Missable. It's RNG based and appears once per save file.
Exact requirements are unknown. What's known is that requires a well which is always placed at the beginning of the game regardless of the map you chose. There's small chance for this event to appear whenever a student plays on top of it. If you already sold it, your only option is trading with Bunny Academy rival school which sometimes spawns on 3rd region. If that fails start new game.

You'll randomly get notified so watch out for every notification thrown your way. Upon receving this event a cutscene will play. Spirit will ask you a question and you have to answer honestly to get the achievemnt. If you answer correctly you'll get 2 talented students with the same aspiraton as student who triggered the event.
Correct answer is Neither


Drake's "Care Package": Accept Drake's deal.
Deal is offered once per save file. If you've already declined it, then you'll need to start a new game. Being low on funds increases the chances of it appearing.

Requires dispatch map unlocked via School reform I reasearch and no admission office built in Theater boulevard community. In following days you'll receive an offer of accepting trouble kids from rich families. Offer can appear even within 1st week.
You need to accept it but actually admitting these kids is optional. It's basicly free admission office without contribution cost for admitting students~




Iron Fist: Send a teacher to stop 10 protests.
The hardest achievement in my opinion at the moment. It's also a quite time consuming.
Students protest when one of their needs isn't meet. You can only have 1 protest per week, so it can take you at least 2 ingame years. Known causes are: not enough restrooms, not enough entertainment, not enough hygiene furniture, dirty classrooms. If you thinking about deliberately not providing multiple needs forget it, because students will faster drop out then protest.

Update #2: on August 10 devs fixed the problem with protests not being able to trigger multiple times, which makes workaround described below reduntant. I'm leaving as it is in case this glitch reappers in future updates.

Outdated: However due to certain glitch in current version of the game there's a chance that no more protest will take place. In order to prevent that you have to save and reload constantly.

Update #3: according to UberPootPoot trick below doesn't work any more but I still leave it for the sake of preservation :)

OutdatedHere's how I did by focusing on making classrooms dirty:

• Once new week starts sell all cleaning equipment around classrooms, then save and reload after taking graduation photo,
  
• wait for red bubble with yellow exclamation mark
  
• once protest pops up send a teacher to stop it
  
• after stopping it save and reload again(just in case save in seperate save slot)
  
• wait for next week
  
• repeat 10 times

Shoutout to ETKnight for helping me dealing with the glitch !
here's an example of how protest looks like:
If you have at least 100 students protest will happen almost instantly. Also you don't have to have 10 protests in 1 save.

Update #1: according to Gamey
You can just keep saving and reloading and get it done in the same week. I tested it myself and it actually works.

Crisis Stopper: Extinguish 5 fires.
Actually tricky one. You very likely get 1 once you built food tent. However you can stop seeing any fires once you upgrade foundations to more fireproof ones. The best way to cause fire is to build couple food tents without buckets or fire extinguisher near them. Not 100% sure but from what I've seen fire hazard protection items makes fire appear less likely. Once fire starts just place water bucket near.
Same as Iron Fist you don't have to extinguish 5 fires in 1 save file.


Protection Squad: Confiscate 30 contrabands.
Similiar situation to Crisis Stopper, but the difference being the students you admit. To reliably Confiscate contraband you have to check students inventories. Most students rarely bring any contraband. To ensure steady stream of contraband accept students from Theather boulevard and Finch bay. Either search them routinely or wait for events such as Frog dash or Secretly gaming, once they're resolved contraband is automatically taken from students involved. if you wanna really speed up this process set up security gates from Peace and stability research.



Elite HR: Recruit an elite teacher.
They sometimes show up in Talent Marketplace. You can easly recognize them thanks to unique portraits and names. The easiest way to get one is to trade with rival schools. Not every school has one but most of them do. You need 85% relationship with rival school and they're quite expensive (they cost from 80k to even 200k)

Throw the money and contribution points until you see green bar.

First Love: Have a pair of lovers in the school.
You are at the mercy of AI on this one. Sometimes you'll get a notification (with a letter in it) about love confession happening somewhere on your campus. If person being confessed to accepts they become a couple. You can only increase chances of love confessions by putting down furniture such as love mails and picnic carpets. Worth nothing that potential couples need to become friends first, so put down benches and select correct snacks in stores too. This will increase positive relations. There's nothing else you can do other than waiting.

Confidant: Have a pair of Confidants.
You are at the mercy of AI again once again. It's much harder to get. 2 students need to reach max level of positive relations without becoming a couple. Same as with First Love put down benches but avoid any intimacy boosters if you've already gotten First Love.

Glorious: Win a game on Hard.
Achieve any win goal while playing on hard. If you survive 1st year you'll manage. You get less money and spent more time waiting for extra funds to expand so pay more attention to your daily balance.




Time is Right: Give a teacher a raise.
Missable due to poor UI. It doesn't count when you accept teacher's demand for a raise. You need to raise manually. Many players can't find staff salaries at all, so below there's instruction how to do it.



Click on 1. Number of staff icon, then 2. Salary bellow close window button.
All what's left is to 3. raise teacher's salary until number is green.




Greedy Grinch: Demolish snowmen made by students
During winter sell one of snowmans built by students. They spawn often so it's not hard to find one.




Closed Loan: Pay back 1 loan.
The quickest way is to borrow 10k and repaying immediately it.






Wonder: Build a Wonder.
Once your school reaches level 5 wonders become unlocked. They have seperate tab in facilities. They cost at least 10k and ~500 contribution points. Also they're built in phases couple of days, so you need to check on them every once in the while.




Boarding School: Build Male and Female Dormitories, and a Dormitory Hall.
Hard to miss if you going for Teaching win but can be missed if you're going for other 2 wins. It's required for admitting 4 star aspiration students. Just build Male and Female Dormitories, and a Dormitory Hall. Size doesn't matter





Skydiving: Build a Helipad.
Same as Boarding School but it's required for 5 star aspiration students.





First-Rate School: Max School Level.
This can take some time. Max School Level is 9. Before achieving last goal of selected win wait for a while.





Relentless Research: Complete all research.
Time consuming. You don't get near it in casual playthorugh. I recommend going for it when you want get max School Level since every research gives you school level progress.

First Practical: Start a new game on Survival Mode.
Nothing to say really, although game refers to Career Mode as Survival Mode.







Internal Promotion: Train a teacher.
You need to train Ms. Lin to teach your first students good enough to pass exams. It's hard to miss. Trained attribute doesn't matter.





Redecorate: Have a 2-star Facility.
Just place additonal furniture. Food tent is particularly easy to upgrade to 2 stars.





Satisfactory: Get an "Excellent" in the exams.
~95% of students have to pass exam. Can be easly achieved in 1st week. If not, then in 2nd you'll get for sure. Pay attention to any warning sings next to classroom's icons.





Orator: A successful speech.
Pick positive options to get at least 60 score. If you're somehow having problems then pick in following order:
Friendly Openning -> Talk about Academics -> Commend/Consolation and Encouragement -> Award bonus





Organizer: Drag a Facility to a Management Facility.
Action is mandatory to progress. The Game explains this well enough. Once you built management office and assign a teacher with required certificate drag any facility under this office.





For the People: Have a teacher with Service Certificate.
Teacher get's after working for a while in service providing facilities. Hard to miss since you need food tent to provide food for students and it's required for teacher to have in order to be assigned to certain facilities such as cafeteria or dorm hall. In most of my saves I had a teacher with one by the time fall comes. Can be also gained by assigning teacher to infarmy, school guidance office, school store or supermarket.




Explorer: Unlock a new dispatch location.
You need to explore unknown areas to get more students and game explains good enough how this works.




Monopoly: 100% control over a Community.
Quite tricky to get with communities on dispatch menu due to rival schools investing every week. You can easly get it with your 1st community. To speed up the proces invest in it's admission office and by the time most students from this community pass you'll reach 100%.





Unforgettable: Take a Graduation Photo.
Game forces you to take on every week whenever at least one 3rd grade class graduates.




Serve-a-Bucket: Punish a student.
Hard to miss but not impossible to. Whenever student's discipline falls below 60% there's a chance they'll slack off during classes. When it happens there's a yellow bubble above the student. Click the student and select Punishoption left his portrait. You can also get it during winter since coal heaters casues students to fall asleep. In current version at 2 students almost constantly.





To the Clouds: Construct a building at least 3 stories high.
Self explanatory. Just make sure you built stairs allowing staff and students accces to it





Jr Architect: Reach Building Score 3,000.
You'll get it at some point while expanding.





Property Dev: Buy a new plot.
Click the red flag on empty plot then buy it





Big Bucks: Save up 100,000.
Self explanatory and it's not hard. Once you reach certain school level you can take 100k ¥ loan.





District School: Reach School Level 5.
You get progress School Level constatantly, so make sure you claim the rewards.





Big Family: Have 100 students.
Really hard to miss, especially if you're going for population win. Every admission office provides max 15-25 students on average, so built a few.





Master Builder: Reach Building Score 8,000.
Past 5,5k getting to 8k might take some effort put nothing particularly difficult. In saves when I got teaching win and facility win I was past 10k mark, so it shouldn't be a problem. Just put down better furniture as you research.




Star Search: Admit 20 students with 3-Star Targets.
Self explanatory.
3-StarStudents can be found on 2nd region on dispatch map after research School reform II. If you're struggling with getting 20 of them, then invest into multiple admission offices and make sure that already admitted 3-Stars pass their exams.

You don't have to play in career mode. There's limited number of wins goals achievable on one save file to 1 win goal per save as Serefina pointed that out.
Possible workaround is to save and reload before getting one of the wins, then reloading to that save after getting an ending. After this you can go for other one.


Population Win: Complete Population Win.
The easiest one to get. There's ~750 students across all communities, so if you're admitting at least 2 communities from every region on dispatch map you should get 250 students in no time. High satisfaction levels isn't a challange neither, just promote positive relations and satisfy every need.


Facility Win: Complete Facility Win.
Pretty much achieved by going after one of other wins. If you're replacing classroom equipment with better ones from research and like to build aesthetically pleasing builds, then it's no problem to get 12k building score. Just remember to build both types of wonders. Wonders are unlocked at school level 5, advance wonders are unlocked between school levels 6-8 and cost ~120k and 1000 contribution points in total to built but with money income at this point of the game is matter of time.

Teaching Win: Complete Teaching Win.
Despite abysmal 0,4% of people getting it it's not as hard as it seems.

It's just the most time consuming win due to requiring end game research and educating students from 3rd region on dispatch map. To explore areas in 3rd region send 2nd grade class because 3rd graders will graduate before reaching their destination. If you're lacking classrooms for 5 star aspiration students in late game, then stop admitting 1 star or 2 star aspiration students and assign 5 star one to their classrooms.
Worth noting that by "Educate" game expects you to teach kids good enough to graduate.

Update: with introduction of clubs you can now level up admission offices - one of the upgrades is increasing aspiration level but it's pricy in contribution points.

DISCLAIMER #2

Some claim that you can achieve other wins while pursuing one, some claim you can't get other ones. If you get the win you don't want try avoiding fulfill goals by:

• Population Win: expelling, failing students on purpose or limiting number of admissions
  
• Teaching Win avoiding admitting high star aspiration students
  
• Facility Win: since advance wonders are built in stages do not fund last stage of construction.

By sure to save often !

Thanks to:

• ETKnight for helping me obtaining Iron Fist achievement.
  
• Gamey for sharing faster method of obtaining Iron Fist achievement.
  
• Serefina for bringing up win goal limitation.
  
• UberPootPoot for bringing up Iron fist reload trick no longer working