I definitely agree that the system is way different to that of Europe or say any other western democratic country. The electoral college and the senate are structured to favour the deep south and the smaller midland states. Not to mention Gerrymandering which both parties make use of, however the Republicans have flipped a number of statehouses in the last two years and in the process managed to redraw a ton of districts in their favour. Some of them are being challenged by the JD and redrawn by the courts but a great majority of them will stand. Then you have the voter ID fiasco which should manage to take quite a few minority voters out.
The main problem Obama has is that he came in on a top and bottom coalition. The top is made up of people with grad degrees and rich educated suburbanites, and in the bottom there are the blacks, the latinos, the gays, and the students. I still think that most of those groups will side with Obama, but it's still a weak base to come in on. He has serious problems with getting his message across to white blue-collar workers. McCain got something like 2/3rds of the blue-collar white vote last election. And from what I can tell it's a crucial demo in quite a few of the battleground swing states like Ohio.
Not true. Yes the moderates have been squeezed out of the GOP. But there is still a substantial group of moderate Democrats. Not to mention the fact that the Democratic party is continually shifting to the right when it comes to economic policy.
You can't seperate out the primary from the main election that easily. Primaries often dictate the sort of policies the candidate is able to run on. Yes he will peel back some of the rhetoric in order to appeal to the independents, but you can only flip-flop so many times. This is Romney we're talking about afterall.
His wealth will be a big problem. I wouldn't downplay the VP selection either. If he picks a capable Hispanic VP like Rubio then he's in with a real chance.