By next Tuesday night, every single voter in the country will have had a chance to cast a ballot in the Democratic primary. You would think at that point that we would have a clear and unequivocal winner in the election. I don't think that's too likely. The problem here is that there are so many competing metrics of success (delegates, states, popular vote) that it's difficult to say which one really determines the winner.
Now, the system is set up so that the delegate count is what really matters. And in that realm, Obama is definitely the winner. Same with number of states won. Where it gets tricky is the popular vote. After all the hooting and hollering about the 2000 election going to Bush because of the electoral college when Gore won the popular vote, it would be a pretty strange sight to see the Democrats award their nomination to someone who had won the delegates, but not the popular vote.
So this raises an entirely new wrinkle. As it turns out, there are all sort of different ways to count even the popular vote. Do you count Florida? Michigan? The caucus states without official vote counts? Puerto Rico, which isn't allowed to vote in the general election?
See? It gets complicated quickly. Added to the confusion is that depending on how things are counted a different candidate may come out on top.
Here's my plan for counting the votes. I haven't done the math or anything to see how this turns out, so this is just me being as fair as I can. For practical purposes, the popular vote is a sort of straw poll that conveys a sense of legitimacy on the candidate who wins it. Haggle over the rules for seating delegates, but the popular vote should be as inclusive as popular. So I say count all the votes. That includes estimates from the caucus states as well as Florida and Michigan. A note on Michigan: given that the Clinton campaign's argument for counting Michigan is that the "uncommitted" voters were saying that they wanted Obama, give him all the uncommitted votes. Otherwise take the state totally out of play. I'm a little mixed on Puerto Rico because they won't be voting in the general election. In that sense it would almost be like taking a poll of Canada and counting that. On the other hand, PR is a U.S. territory and they're allowed to vote, so let's count 'em.
Add up all the votes and let the chips fall where they may. What a crazy election.