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That was an amazing write-up! Thank you so much for explaining. It’s reassuring to know that in some ways I was overthinking things, and to have those tips for the little things that I didn’t know. I guess beyond that, it’s just a matter of RNG, right? It doesn’t matter if I use the best strategy against the mouse whose target is a 12 if he keeps drawing 10s. XD

Yep, RNG is a huge factor and your biggest way to mitigate it is to bet low. Only time you can't do that is against enemies with Ante-Venom (wow that pun hurts even after all these years).

How low should I bet? I’ve been betting maximum every time. I thought it’d take forever to win if I went with low bets.

Up to you, I think I usually aimed for a certain percent of the chips I had. That way if I did poorly I'd decrease my bet and if I did well I'd increase my bet. The larger percentage of your bankroll you use, the higher likelihood that you run out before ever seeing the positive returns. This is tied to the concept of 'risk of ruin' in gambling/stock trading.

Oh, good to know!I think my only other question is about Risk Taker. It says that it lets you bet money you don’t have. However, I don’t think I’ve ever seen the game let me bet above my maximum chips, unless I’m splitting/doubling. Am I missing something?

Had to pop open the source code to remember, looks like it lets you double or split even if you can't afford it. Honestly that sounds pretty weak, but maybe there's synergy with that card that lets you keep doubling/splitting even when it wouldn't make sense.