Missing: Republican warchest
IMO the problem with Hillary and Obama - strictly from an electability view - is that they would ensure that the 2008 election is fought in the same states as the 2000 and 2004 elections. Which mean - Iowa, Michigan, Pennsylvania, Wisconsin, Minnesota, New Mexico, Ohio, and Florida.
Only the last two are states that Bush carried - so the bulk of the fighting will be on the Democrat's turf. That leaves little room for error, and that was a big reason why Kerry lost.
I see the same thing, maybe even worse, for Hillary. She will have to campaign heavily in Michigan, Pennsylvania, Wisconsin, and Minnesota - states that should be solid Democrat. My guess is too that Florida will be even less in play than it was in 2004 with either of them. So the GOP will just campaign heavily in states won by KErry and also in Ohio. IT sets up too nicely for them.
I don;t know what candidate from the Democratic party could change this. You really don;t have anyone that comes off as a BLue Dog Democrat - the type that did so well in the 2006 elections in otherwise solid red states and districts. Richardson, I guess, is close - but from what I have seen of him so far he is goofy in debates and on the campign trail. Edwards' economic populism might be able to make inroads into a some red states, but I doubt it. Chris Dodd is a solid guy, but he is too much into details to be a presidential candidate (sort of like Kerry). Biden might be the best guy from an electability standpoint.