For all these reasons, gentle readers, I urge you to wire some money into an offshore account, log into intrade, find some outcome that would make you miserable, and bet heavily on it.
Degree of caring isn't actually the thing that makes insurance worthwhile.
Find an outcome that would make you financially miserable, and bet on it such that if it comes to pass you won't be financially miserable. In a sufficiently non-rational market (ie people betting on things because they want them to happen) the size of the bet will not make you financially miserable if the outcome doesn't happen and you lose the bet.
I think this is the core idea of the post, and the stuff under the headings is some of the positive results of this course of action, not necessarily a justification for it.