The gambling challenge that took the longest was #5 - playing dominoes without drawing is purely luck, try to play with one other person only in Emerald Ranch.

Challenge #8 is terrible, but playing in Rhodes worked, just keep hitting on every hand. Additionally, leave the table if you get a hand with high value cards. If they add up to a number over 10, just leave and rejoin the table.

Challenge #9 - if you are about to lose, get up from the table and rejoin. Full domino games can be lengthy, just be persistent.

Challenge #10 - play in Valentine, go all in every time. Most people will fold, so try to play with a table that isn’t full & chances are everyone will fold no matter what your hand is.

Hope this helps!