Very cool idea, I like the constant prompts to gamble. Maybe it's just kind to me because I'm new but I won every single one. It's given me an idea that maybe you'd find useful. Imagine if you could negotiate the size of your gamble with the AI. Like on a turn, you get to choose the ranges of your gamble, say "I either move 2 backwards or 20 forwards with 50 50 odds" and the AI would be like "no." so you don't get to move that turn.
But if you said "5 forwards or 5 backwards with 10 90 odds the AI would be very happy to let you make such a stupid risk.
I dunno, I think there's a lot that can be done with this.
My only complaint would be that there was so much time spent shaking and waiting for the AI to go and not much time actually playing and making decisions.
Nice work though, it would be interesting to see where you take this