Obama is not going to win Florida. The two parties were about dead even in the last two elections, but circumstances are different now. Not only did Obama cause a stir among Floridians with the whole primary brouhaha, but Florida also has a large elderly population that's going to strongly favor McCain. None of the polls in recent months have bode well for Obama. I think we can safely consider Florida a red state this time around.
Pennsylvania, however, will probably be going Democrat. It might be a close one with the rural Appalachian population in the middle, but Pittsburgh and Philly should be blue enough to negate that. Things are looking significantly better for Obama than McCain here, and I feel pretty confident the Dems should be able to secure it.
Iowa and Wisconsin have been swing states in the past with very close results, but Obama has a decent lead in the polls, he won both their primaries, and his geographical proximity should give him an edge. I consider it rather unlikely that McCain will make a comeback in either state, especially considering he has bigger fish to fry elsewhere and a more limited budget to work with.
Here is how I think the scene looks right now.
McCain should win Alabama, Alaska, Arizona, Arkansas, Florida, Georgia, Idaho, Indiana, Kansas, Kentucky, Louisiana, Mississippi, Montana, Nebraska, North Dakota, Oklahoma, South Carolina, South Dakota, Tennessee, Texas, Utah, West Virginia, and Wyoming for 201 electoral votes.
Obama should win California, Connecticut, Delaware, Hawai'i, Illinois, Iowa, Maine, Maryland, Massachusetts, Minnesota, New Jersey, New York, Oregon, Pennsylvania, Rhode Island, Vermont, both Washingtons, and Wisconsin for 238 electoral votes.
That leaves just nine states which could, I think, go either way. McCain needs 69 and Obama needs 32 electoral votes from the following to win:
Ohio (20): Polls are showing Obama and McCain neck-and-neck here, with Obama retaining a small (read: statistically insignificant) lead. The predictions market is going more strongly in Obama's favor, but that doesn't necessarily mean anything. If McCain is going to squeak out a victory, he needs this state. Obama has a few options without it, but McCain pretty much loses the election if he loses Ohio.
Michigan (17): A traditionally blue state, but the margins for Democratic victory have been getting narrower and narrower over the years. Michigan's big cities are shrinking and the more conservative regions like Grand Rapids have been growing in political importance. McCain may very well take this state for the Republicans for the first time since 1988.
North Carolina (15): A traditionally Republican state that McCain should win, but polls are showing Obama rapidly catching up. North Carolina's large black population just might tip the scales in Obama's favor, or at least put up a good long fight that will divert McCain dollars from other states.
Virginia (13): Another traditionally Republican state that has suddenly come into play thanks to Virginia's large black population and the growing suburbs of Washington, D.C. Polls show Obama and McCain tied. The Democrats could definitely take this one, especially if Jim Webb is the VP candidate.
Missouri (11): Considered a very reliable benchmark state, meaning it almost always votes for the winner of the election. Polls show no statistically significant lead for either candidate here, but Obama hailing from a neighboring state may give him an edge.
Colorado (9): Voted Republican in the last 3 elections, but polls are showing Obama has a good lead he might very well be able to hold onto till November.
Nevada (5): A traditionally red state, polls show McCain with a bit of a lead, and his geographical influence could spread into Las Vegas enough to significantly counteract the urban Democratic vote. I'm predicting a Republican victory here, but not by much, and I wouldn't be terribly surprised if Obama narrowly wins Nevada.
New Mexico (5): Again, there's the question of whether McCain's geographical influence can cross the state border. But polls show Obama with a modest lead, and he's very popular among Hispanics, which make up enough of New Mexico's population that it's the only state in the union where Spanish is an official language alongside English.
New Hampshire (4): Voted for Kerry in 2004 but for Bush in 2000. Really difficult to say which way it'll swing this time as it's a state with a peculiar political climate, but if it was blue enough to vote for Kerry I'm hoping it'll also vote for another Democrat who's a little more exciting than Kerry was.