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I didn't mean to imply nonlinear functions are bad. It's just how humans are.
Prospect Theory describes this and even has a post here on lesswrong. My understanding is that humans have both a non-linear utility function as well as a non-linear risk function. This seems like a useful safeguard against imperfect risk estimation.
If you setup your books correctly, then it is guaranteed. A dutch book doesn't need to work with only one participant, and in fact many dutch books only work with on populations rather than individuals, in the same way insurance only guarantees a profit when properly spread across groups.
Insurance makes a profit in expectation, but an insurance salesman does have some tiny chance of bankruptcy, though I agree that this is not important. What is important, however, is that an insurance buyer is not guaranteed a loss, which is what distinguishes it from other Dutch books for me.
Prospect theory and similar ideas are close to an explanation of why the Allais Paradox occurs. (That is, why humans pick gambles 1A and 2B, even though this is inconsistent.) But, to my knowledge, while utility theory is both a (bad) model of humans and a guide to ho... (read more)