With a few exceptions (such as Vermont), "blue states" mostly turn out to be red states with a couple of big blue cities (Pennsylvania, for example, or even California). Almost by definition, an effective conservative executive - the kind you might want in the White House - can only come from flyover country.
So, when a conservative pundit mocks Wasilla, he's mocking conservatism as it's actually lived, as opposed to conservatism as a theoretical fantasy playground for the purposes of cocktail-party banter.
Ladies and gentlemen, Steyn hits it on the head. Kristol, Noonan, and others have become more and more out of touch. They are too concerned with looking good in the press or being the toast of the parties than in REAL conservatism. That is why Palin gets so many thousands at her rallies. She is real, not some Park Ave. conservative who writes conservatism but doesn't live it.