Barack Obama is cooler than the other side of the pillow...and this is a bad thing.
Yglesias talks about how narratives are formed, but the problem is that the core narrative of presidential politics is still focused on two simple ideas:
1.) Republicans are successfully communicating with the American people.
2.) Democrats aren't.
It's why the "liberal media bias" meme is so pervasively powerful - it allows for the idea that liberalism has this massive organ which is constantly communicating with the American people and failing, as evidenced by Republican equivalence or even superiority in gaining power. Whining works, because it's both interesting and allows the media to genuflect on what's most important: themselves. In terms of Obama's candidacy, it's about engaging in something that he's shown flashes of getting, particularly in the case of John McCain's houses. It's flooding the zone, not just making a complaint something that is directly traced back to Obama, but instead creating a backlash that causes our 24-hour news media to take it for granted that they're probably fucking up and pissing off the American people, as dictated to them by a major political party.
The issue's never this foul, it's always the next one.