The real question is whether the pick will continue to look like a highly political choice. If McCain and Co can keep attention away from the actual work Palin has done, then they have a good chance of making a very close election (I say close, because there's still a lot of work to be done). In that regard, I think all the personal stuff about Palin's daughter may turn out to be helpful. If the McCain camp can keep pointing out (quite correctly) that the pregnancy of her teen daughter is essentially a non-issue, then they may get away with ignoring other (legit) critiques. That is, whatever hit Palin takes for her pregnant daughter has already been inflicted- talking more about it isn't going to hurt the ticket.
Finally, I'm not familiar with Nate Silver, but Sullivan brings this summary to my attention:
You have Mitt Romney -- one of the wealthiest men ever to run for office -- critiquing east-coast elitism, and Mike Huckabee -- who is an economic populist in disguise -- critiquing big government, and Sarah Palin -- who voters don't know one iota about -- critiquing Barack Obama's biography.
