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ygrt comments on Iterated Gambles and Expected Utility Theory - Less Wrong
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The option A could be justified if you take into account emotional utility. Therefore you might trade 10$ for avoiding the regret you will feel in 75% of cases if you choose option B. This could hold even more true for larger sums.
By the way, I would choose option B because I don't think this self-indulging attitude is beneficial in the long run.