This gambling addict simulator fits the theme extremely well. As you can spend time to improve both gain per turn, chance of winning and win multiplier there is surprisingly much depth for such a simple game. Also, the visuals are consistent and the game is fun. I found myself looking for clues on exactly how much I could influence the chance by my choices but maybe it is best unknown. It's up to chance anyway and if you don't risk everything, you might not win enough to beat the bosses.
(Beat the game in 125 days)