Remember that Silver is running a monte-carlo type model. In his case, what his 'odds' mean are that when he runs the simulation N times, 70% or so of the times, Obama wins, 30% or so Romney wins. So its not "I'm 30% confident the outcome of the model is wrong" its that "30% of the time, the model outputs a Romney victory."
Okay (though to me that sounds like he has many related models that differ based on certain variables he isn't certain about... maybe that is being pointlessly pedantic) but would you agree that a R victory would be evidence that the model needs adjustment, stronger evidence than that the model was was reliable as is? If not, what if it was 99 to 1, instead of 60 to 40? Just trying to clarify my own thinking here.
From Ezra Klein:
Okay, technically, winning the money would be very weak Bayesian evidence that the initial probability estimate was wrong. Still a very good quote.