If you look at the big picture, Obama basically has to outspend McCain twice to get the 100 EVs in the seven swing states (FL,OH,IN,NC,VA,CO,NV). Out of these, FL,NC and IN are very close. In Ohio, conservatives just sat home. In Colorado,Virginia and Nevada Obama recruited massive number of voters and got them out to vote. This is what happened in a nutshell. He couldn’t budge the red votes in Georgia, Montana and Missouri enough to get a landslide. He should really be worried because if his cronies don’t get the unicorns and rainbows he promised it is going to get ugly.
Except, once he's in, it's hard to unseat a politician. I think the last president that ran for reelection, that didn't make it, was Herbert Hoover.
Of course, Truman and LBJ saw their polls slip and decided not to run, so I guess we can still hope.