Related to the flake thing.
Why would Obama take a position that can easily be seen as Infanticide and other Pro-Choice Dems would not have a problem agreeing too?

From the Corner.

Obama is the agent of change and compassion. He can heal the planet and lower the oceans. By stating that he would've voted for the bill had it contained the neutrality clause, he conveys that he supports the principles of the Born-Alive Act. Yet he takes no action whatsoever to make it happen.

Therefore, even if we accept any one of Obama's explanations regarding his vote against Born-Alive, we're holding him to an incredibly low standard for someone who intends to lead the nation. If he supports the principle of Born-Alive, the question isn't why he voted against it — the question should be, "Sen. Obama, given your education, skills and background why didn't you take the relatively simple step of amending the draft so that the bill would work?" Isn't that what we expect from a leader?
Obama voted "present" more than 100 times in the Illinois state legislature. Why did he rouse himself to vote "No" on this one?

Emphasis added, and that's the real question.

And here's more

In fact, it's not. Regardless of what Obama's personal beliefs on the matter are, he voted against legislation that would have protected the rights of children who survived an attempted abortion. That fact is so stunning, and the implications so brutal, that Beckel and Colmes simply could not process it. They assumed it had to be impossible. But it's not only possible, it's true. Obama cast the vote he did. And it's clear from last night's exchange that Democrats understand how explosive this issue can be.
It doesn't help matters, of course, that Obama's story is falling apart. Obama has been insisting that if the wording of the Illinois Born-Alive Infant Protection legislation had been similar to the wording of federal legislation, he would have voted for the legislation. But as the Washington Post reports today, "Obama aides acknowledged yesterday that the wording of the state and federal bills was virtually identical."
Oops.

So not just a flake but a lazy one too.
Again this was low hanging fruit. Obama could have bulked up credit with both the Pro-choice and Pro-life groups and shown his legal skills and had a bill under his belt.
Why didn't he do that?