SoullessAutomaton comments on Rationality is Systematized Winning - Less Wrong
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I like your definition of an accidental win, it matches my intuitive definition and is stated more clearly than I would have been able to.
Yes. Actually, I think the "In cases where the expected value of an action is unknown" clause is likely unnecessary, because the accuracy of an expected value calculation is always at least slightly uncertain.
Furthermore, the second-order calculation of the expected value of expending resources to increase epistemological rationality should be possible; and in the case that acting on a proposition is irrational due to low certainty, and the second-order value of increasing certainty is negative, the rational thing to do is shrug and move on.