He's dealing with terribly sketchy data. Response rates to political polls in America are south of 10%, and there's no proof that the portion of the population willing to have a conversation about their political preferences with a stranger is representative of the population as a whole.
He's also dealing with incomplete data. The 'likely voter' screen pollsters use to determine who's actually going to the polls isn't always revealed, and it varies from organization to organization. Polling is a cash-strapped industry and some polls' likely-voter screens are much more porous, cutting down on staff required and voter contacts needed to generate a 'statistically-significant' sample. But details of the likely-voter screens and response rates aren't always available.
His results are also completely unverifiable. Let's say his final prediction is 80-20 in favor of one candidate, but the other candidate wins. Well, his model did say that'll happen one time in five, so you can't really criticize it.
The appropriate amount of precision to conclude with, given all of the fuzzy inputs, is something like 'well, we can't tell who's going to win - it's close, although this one candidate's chances look slightly better'. It's not 'Candidate A's chances improved from 74.6% yesterday to 76.5% today'.
That's what makes Nate Silver so irritating - he doesn't know any more than the journalists, but he claims he does.