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wedrifid comments on Buy Insurance -- Bet Against Yourself - Less Wrong
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I came very close to making a large bet against Prop 19 passing in CA, because the universe where marijuana was legalized would have been A very desirable place for me and my business to find ourselves. If the US Department of Justice was busy suing California they wouldn't have the resources to spend on scheduling kratom.
Alas, I didn't (for the same reason I have never bet on In Trade, hyperbolic discounting, basically... I want to make my bet right now, not wire it and wait a week), so I am several thousand dollars poorer than I would have been and marijuana isn't legal in California.
I'm also reluctant to buy not-Obama futures right now because I think Obama's chance of winning is closer to 75% and that the market will correct itself eventually and I'll be able to buy right around the inflection point.
This would seem to suggest that it would be rational for you to be selling not-Obama futures now. Until the market reaches your prediction modified by your risk-aversion incentives and overhead.