As long as you don't connect to a VAC enabled server there's no way for Valve to know you're running Idle Master. Idle Master effectively sits at the start screen of the game, it never connects to a game server.

If you try to play CS:GO while running Idle Master in the background you'll run into problems.

Due to changes in the refund policy you now need 2 hours of playtime before the normal STC drop time starts, most games will start dropping at 2.5 hours of playtime and every 30 minutes after (Devs can increase the 30 minute timer and there is an element of chance). Your games pretty much fall into either having well beyond the time needed to receive their cards(E.G. Cities Skyline with 12.9 hours) or not enough (lots of 1.6 hours). Likely it's a connection issue that a lot of other folks have reported, or we're working off different definition of "on all night"

When you start Idle Master, how many games does it say have drops remaining? How many games on your your Badges page have remaining drops?

For non-F2p games, yes. For F2P games you must spend $9US in the game's store for each card drop.

Double check your Badges page to see if you have drops remaining. You have enough playtime in CS:GO to have received all of your free drops and it looks like the only non-F2P game you have.

Yes, idling some more will result in you receiving some cards.

To prevent abuse of the return policy, you now need 2 hours of playtime before the normal drop rate starts. Most games have a drop rate of ~30 minutes so the first card will typically arrive around 2.5 hours of playtime. You have 2.1 hours of playtime in Arma3 so you stopped idling it a bit before you would receive some cards.

If you want to pad the playtime for F2P games, the Idle Master FAQ has info on doing that.

If you want to earn cards, first step is to spend $9US per drop and then you can run Idle Master as normal.

Once you have received all the drops from a game that's it. There is no way to gain more drops.

Idle Master will not prevent you from playing other games. I would recommend avoiding VAC enabled servers in case they flag Idle Master as a cheating program.

Running multiple games will reduce the rate you receive cards, so it might not be worth it.