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DSimon comments on Buy Insurance -- Bet Against Yourself - Less Wrong
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The point isn't to make irrational bets, but rather to make rational ones. Ones where the odds you're getting are reasonable, and you're ensuring a certain wealth/happiness minimum for yourself.
Just because you consider it GOOD if Obama wins doesn't mean you can rationally conclude "Obama will win". In fact any way that you can conclude an Obama victory from your liking Obama is obviously irrational.
However concluding that Obama losing will cause you to have financial difficulties means that insuring yourself against such a loss is very useful.
Unless of course you are the CEO of a company with a large contract to manufacture computerized voting machines. In that circumstance, you could also conclude a not-Obama victory if you don't like Obama.