The most difficult part of this is getting him the nomination - given his affinity for retail politics, it'd probably have to be an Iowa win, and that seems unlikely. If he gets it, though, he should win the election. 2008 was probably always going to be a Democratic year, and he can counter two of McCain's main selling points: experience, and expertise in foreign policy. Lower turnout means he probably doesn't do quite as well as Obama, but it'll be a solid win.
VP-wise, I think he'd be inclined to pick either a woman or a minority, in the hope of increasing turnout. Obama's actually a possibility.