I think something that touches closely to what you're trying to do is Rational Poker, which is using poker to train your bias overcoming skill. Specifically the This is what 5% feels like. exercise. The idea is that you can combine your explicitly calculated chance of winning a hand with your gut feeling enough times that they begin matching up. You'll eventually understand what 5%, 10%, 50%, or 90% actually feel like from the inside. Unfortunately, Im uncertain how well this gut feeling generalizes, so using it to determine probabilities outside of areas you've trained it for may be less successful.
Previous Open Thread: http://lesswrong.com/r/discussion/lw/k94/open_thread_may_19_25_2014/
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