I'm not sure if I'm doing something wrong, but I have not been able to beat Amy at blackjack for her level 2 event. I don't know if the card draws are all up to chance or for some reason I am meant to lose $10 every time I play
It's completely random. I managed to win about once every 10 attempts. But now there is a way to get luck stats to make these challenges easier. To do this, you need to complete all the main events of the current Act before the major events. But since you've already come quite far, to make the task easier, you can save before talking to Amy to start the game and, if you lose, load that save.