Coacher comments on What makes buying insurance rational? - Less Wrong Discussion
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Having this in mind, could it be possible to construct such roulette betting system, which have positive expected utility value?
Not if the marginal utility of money decreases as you have more.
If your utility function has convex parts then it might be possible, though. If you have $1000 but owe the Mafia $2000 and they're coming to collect, betting it all on black might be a good idea.