Ironically, I recall thinking the exact opposite after seeing a "Barack Will Invade Pakistan" on the evening news last night -- hypotheticals are so unfair and misleading. I agree that they can be useful questions, but only if we are cautious enough to distinguish between how a person thinks, and what they will actually do. I don't think this is true of the media and general public.

Answering a hypothetical is a two step process: we must first construct, for ourselves, the details of a scenario (a test of the imagination); and then decide what we would do (a test of the problem solving skill set). But the human imagination is notoriously unreliable (for a compelling argument, I'd suggest Dan Gilbert's Stumbling on Happiness). Mental constructions of a hypothetical scenario are painted with broad strokes. The importance of various factors are distorted. Important details are left out. Now this is probably less a problem for the answerer (Obama should -- as a presidential candidate -- be spending considerable time on these scenarios and getting them, more or less, right) than it is for those judging the answer. As an audience, we too must use our imagination to construct our own details of a scenario by which to assess the answer. Looking backward in time is manageable (e.g., the Iraq war question), but looking forward, our imaginations are likely to fail us. If the candidate is at risk for wrongly predicting his/her future scenario, we are even more likely to get it wrong when we judge them on it.

Sure, the hypothetical is a great way to see how someone thinks. But when (and this is sad) was the last time that a president was elected because he had a great imagination and superb analytical skills?

You have a point about the limitations of hypothetical questions. But all questions about the future and what the candidate would do as president are hypothetical questions. And if we don't ask such questions, we won't know what the candidate would do as president.

The problem is that the further the question is from the world as it is, or the world as the candiate understands it, the more likely it is that the answer to the question wouldn't match the choices the individual would actually make. And that's a fair concern.

But the appropriate response for a candiate with such concerns is that the issue is too complicated or too remote, rather than "it's a hypothetical." Of course, then they don't sound so smart. But when they whine about not wanting to answer hypotheticals, when we're trying to figure out the answer to the big hypothetical "would I/my family/the country/the planet be better off with candidate x as president," it just feels like they're blowing off the voters. To me, anyway.