Aren't there other ways of reducing attachment to individual outcomes that are not quite as expensive as making irrational bets? Can't you just become not quite as attached?
Surely piling crazy betting behaviour on top of crazy beliefs is not to be recommended.
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.