Mostly I look at the election on a Macro level.
What does Obama bring that Kerry didn't? If Obama can't deliver more than what Kerry did, he will lose.
Democrats already take the 90% Black Vote support for granted. Barack's ability to eek out maybe 1 percentage point more of the black vote than a white Democrat is likely insignificant. Barack's black factor comes down to total turnout impact. If 90% of every single non-convict black 18 or older voted for Obama that in itself should be worth about 25 million votes. The question becomes electoral college. If Barack attracts enough blacks to turn a red state blue, McCain will have a tough time beating him.
If he just brings out every black in a guarenteed Blue state, it's rather pointless electorally.
That being said, Barack's utter shadyness to any white male voter paying attention is a huge turnoff. Nobody cares about being called racist since they've already played that card over and over again in the primaries. It's already lost its magic and if anything pushing it further is going to backfire. Whether Democrats want to admit it, mist voters don't care about the novelty of a candidate, especially if novelty is their only selling point.
With a wafer thin resume, a nasty habit of backtracking on every issue except universal health care (a general election loser), shady asssociates around every corner, and a general lack of anything except vacuous campaign slogans, basically any coherent voter will ask "where's the beef?" and find it lacking.
I honestly don't think it is mathematically possible for Obama to beat McCain. The Dem primary has fractured their party to the point where feminists are pissed off that the nomination was "stolen" from Hillary, and trust me, feminists never get over their own egos. A lot of Dems are angry at him and either won't vote at all or will pull the lever for McCain.
In short, Hillary basically did what I thought she would do: drag Barack down to the depths of hell if he even thought about messing up her presidential nomination. Essentially its a matter of whether Barack can make up for what Hillary (and his own incompetence) cost him.
And again, as much as the base doesn't like McCain, faced between him and the walking disaster zone that is Obama, it's likely they'll hold their noses. I know I will. I can't even figure out Obama's policy because he keeps changing it every single week. What I do know is he fully intends to cut our defense, build massive entitlement programs, and engage in paper rabbit/harshly worded complaint strength foreign policy. (e.g. :
http://www.youtube.com/watch?v=QnTaWTfwsFU " I will not weaponize space(wtf?), I will slow our development of future combat systems").
Just an aside, please tell me when McCain swung hard right? I must have missed it, cause he's still a centrist from here, his only "hard right-wing" stance so far is foreign policy that isn't appeasement writ large. He really needs help with economics (Obama isn't any better), and his social policy is mostly conservative although he's been more of a cheerleader than an activist. His global warming crap is aggravating and don't get me started on amnesty.
But again, the alternative is the bleeding moron in the above youtube link, who is either so ignorant, so naive, or so arrogant as to believe if the US unilaterally disarms ourselves and cripples our military capability with a huge unneccesary bureacracy our enemies will follow our lead.