I would tell them about the $ in every case. I would feel like a thief if I didn't. I don't really care that they found a way to exploit an edge and rake our poker games, that's no reason to steal.
On the other hand, I usually don't feel bad at all about cheating on tests if I have the opportunity. This is because I feel like grades are extremely overrated and I personally don't feel too bad about getting a decent grade in a class without much effort, if the class does not interest me. In classes that do interest me and that I care about, I would pass up the opportunity to cheat and get what I deserve if I felt I was properly taught the material.
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"Suffer the pain of discipline or suffer the pain of regret"
"Rome wasn't built in a day"
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