I really like your post, CP. I really, really do.
With that being said, I worry that the Obama camp and many of his supporters are being overly optimistic at his chances of winning. McCain has been in Washington DC for as long as he has because he knows what it takes to thrive there. I don't think he'll be bashful at all in his campaign. There will be a late in the game card played by him or some Swift Boat-esque PAC that I feel Obama's camp will be unprepared for. That is what worries me. That is what causes me to watch his speech with a glaze over my eyes. It's a great speech, he's a great speaker but will he be able to overcome what will inevitably be thrown at him? I don't know.
I think what Obama and his supporters should be doing is looking at this whole thing as a huge challenge and not be as assured in themselves that winning is no problem. They need to look at this from the eyes of Karl Rove and think about what someone like him will be throwing at them and hitting back with the same intensity. That is the way to win.