Pentiment

You can spend a "few hours" in Act II buying beer for everyone at the inn. Just speak to Niko after this act's big crime. Once Andreas has made his toast, walk left until you can interact with Hans, Samuel, and Fabian - sitting together playing cards. While tedious, I got this with patience and early game preparation. I had the rapscallion background which allows you to cheat. I believe the logician background can help by revealing the odds; which might speed up this process when used in conjunction with rapscallion (I was not a logician, however).

All you have to do is FOLD every time you are NOT dealing, and CHEAT (without getting caught) everytime you ARE dealing. It might take awhile, but this "strategy" worked on my first attempt of applying some patience. This was after multiple attempts of trying to shorten/simplify the process or win legitimately.

I would also take note that with the rapscallion background, you can sucker punch Samuel during this same event at the inn to unlock the "Should Have Seen the Other Guy" achievement. Just choose [Start punching] when prompted after the fight starts, then choose the rapscallion bonus choice when Samuel speaks to you shortly after. I'll also mention that you will achieve "Down to the Last Pfennig" for placing bets until you lose everything. You would have to be unbelievably lucky to accidently win everything. Just close your current save file, then resume. The autosave will place you right before speaking to Niko.

Good luck.

In ACT 2 when you talk to Nico and he suggests you let everyone drink some beer to loosen their tongue.
After making your speech about Otto, go to the left until and talk to Samuel. He will teach you how to play.
Pass as soon as you see someone else having the same card as you. Keep betting as long as you do not see the same card as yours in the deck at the bottom left corner.
If you lost everything and got the achievement for that, simply quit the game through the guide menu and load back in. You will have to repeat the speech about otto tho.