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McCain may own 1000 homes; so what? There’s no showing he got any of them illegally or as a result of shady political deals. Obama is vulnerable here. I’m scratching my head. Could he really be that stupid to not see this response from McCain? What strategy is being pursued by his campaign?

McCain's response to the original question was the most correct, reasonable one he could give, referring the reporters to his staff for the details. Cindy is a lot wealthier than he and apparently owns a number of condos, possibly under various arrangements, maybe including partnerships or LLCs. If McCain had tried to give a simple answer to what's really a fairly complex legal question, including the issue of "ownership," he was almost sure to get some details wrong and be accused of lying. Hence, the referral to staff people who could give an accurate answer was the right thing to do.