Obama's Disadvantages:
I agree with co-blogger Ilya (below) that McCain started this campaign with some serious disadvantages, and one can argue that it's surprising that the presidential race is as close as it is.
On the other hand, consider this: Kerry, Dukakis, Mondale, McGovern, and Humphrey. Those are the last five northeastern or midwestern liberals to win the Democratic nomination. Moreover, no Democrat has won the presidency without at least one member of the ticket being widely perceived as closer to moderate than to liberal since at least 1948, perhaps 1940. (I don't know enough about how Truman was perceived in 1944, or his running mate in 1948).