I expect we'll see a number of these kinds of articles over the next week or two, retrospectives on what mistakes the Clinton campaign made and whatnot. I think it's important to acknowledge that the Clinton campaign's strategy was not a bad one--it's one that works, more often than not. She had name recognition, a huge war chest, an historic candidacy, and institutional support among powerful party factions, and I guarantee you that any candidate would rather be in that position than in the shoes of any of her opponents, including Senator Obama's.
Atrios is right when he points out that if she'd been on the right side of Iraq, this probably isn't even a contest, because a lot of early Obama support grew out of the fact that he stood with anti-war people at a time when we were all alone, and while I supported Edwards in the primary--his reversal on the war, his acknowledgment that his vote was an error, and his rhetoric on working class issues won me over--I was always attracted to Obama's campaign for that reason.
But even so, there's a reason insurgent campaigns don't usually win, and that's because the institutions mean a lot in terms of organizing and driving voters, so while it's good to look at what the Obama did well in terms of organizing and motivating new groups of voters, and trying to replicate some of that down-ticket and in future campaigns, it's also important for future candidates to acknowledge that campaigns like Obama's come along maybe once in a lifetime, and that if you're running, better to be the person with the advantages. It might be more exciting to come out of nowhere, but nowhere is also where you're more likely to wind up.