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The problem Obama has isn't like you say a simple equation that either you get it or you don't. It's that a hell of a lot of us aren't buying it.
Maybe we're not tone-deaf but rather hearing the subtones that come with age and living in a real world that the affluent and the young don't.
I do think that you are right about the "Cool Kid's Club". It is cool to be a rebel and take a stand that is against the "Establishment",and it is very much a Club". Liberal guilt is a very real thing and the chance to stick it to the older generation is too much to bypass.
