Right off the bat, I should note that I don't have any particularly great skill at this. But then, neither do the vast majority of the talking heads on TV.
I think there's an 85% chance Sen. Obama will win. That's been my number for most of the election season. Right after the 2006 election that number was at 90%. If Sen. Clinton was the nominee my estimate would be at 80%. The only time I've felt the number was 80% was during the most recent dip in the polling, for what ever you want to make of that. By comparison, I thought 2004 was a 50-50 shot, and I thought 2000 was 70% likely for Gore. I figured no way America would be dumb enough to vote for Bush, and while on the raw numbers I was right, it was close enough to steal.
Here's my current - and by current I mean right at this hour, it changes regularly depending on my mood and what I've had for lunch - map of how I best guess the election will turn out.
In this scenario, Sen. Obama would win 286-252, which funny enough is the result of the 2004 election. Right now I also think Sen. Obama will win the popular vote, thanks to his strength in big population states like CA and NY as well as increased black turnout across the board in places like GA, NC, SC, MD, LA, AL, MS which won't help the electoral college but help the bottom line. Electoral-college wise I think the black vote will help in Michigan, Pennsylvania, and Virginia. And the Hispanic vote in NV, CO and NM. I gave OH, NV, and FL to McCain in this map, though I could see either of those as Obama states, while I think McCain could flip NH or MI.
This is just a guess. And gut feeling. Anything can happen.
And purely for giggles, this 383-185 map is what Obama supporters dream of or see when they're drunk as a skunk. A snowball's chances in hell are far better than this happening, but a guy can dream.