Clearly the point of the infamous Romney bet was that this wasn't supposed to be a trivial amount of money; c.f. the kids on the playground at the nearby elementary school who like to say things like "I'll bet you a million dollars that...." None of them have one million dollars; many of their parents probably don't even have a million dollars. (It's Arlington, so the number of their parents that do is probably non-trivial.) Still, the point is that they are so sure they're right that they're happy to frame the bet as one that cannot possibly be lost. Robin Hanson, however, harrumphs further (and convincingly) about what is really going on here:
The idea that a president candidate couldn't afford a $10,000 bet is crazy, as is the idea that ordinary folks don’t know this fact. They pay for TV commercials, which cost lots more than $10,000. They fly all around the nation in planes, which gets expensive.
So clearly we have moved high up into belief meta-levels here. “Yes, most people know Romney can afford $10,000, but some aren’t sure that most others know this, and so this shows that Romney doesn’t know about such folks.” Or “It is rude to point out that you are rich, even when everyone knows you are rich. Yes wearing nice suits shows he’s rich, but not wearing suits is socially unacceptable. Offering smaller bets is acceptable, however, so offering a big bet could be interpreted as bragging about wealth. Not that I’d interpret it that way, but someone might, and this shows Romney doesn’t realize that.”
Geez it must be a pain to be a presidential candidate. This all shows how much we care about social savvy and signaling in such folks. We don’t much care if they understand supply and demand, but they damn well better know who might try hard to be offended by what.
Yep, that's pretty much it.