It’s tempting, at first glance, to see the attacks on McCain’s house counting problem as trivial gotcha politics. Even assuming that’s true, I won’t shed many tears at this point — not after watching McCain rip Obama every day for the last month for excessively silly reasons. But there’s actually a substantive component to Obama’s attack — that is, there’s a reason why this stuff actually matters.
It’s not that being rich makes you adverse to the interests of working people. I mean, I suppose there are real-life Montgomery Burnses out there, but that’s not the issue with McCain. In his own head, I suspect he would sincerely like to help people.
The point, then, of the attacks is not to claim that McCain’s heart is in the wrong place, or that it’s two sizes two small, etc. The point of the attacks is epistemological. Being that rich for that long puts you in a bubble. Life is the sum of your experiences — the aggregation of your sensual interactions with the things around you. If you live in the world of the super-duper rich, that’s necessarily going to affect how you see the world.
And that's why McCain’s super-wealth is relevant — it shapes the types of experiences he has had on a daily basis. If you’re that rich, you never viscerally worry about losing your job. You never experience the anxiety of not having health care. You tend to be surrounded with rich people who have their own narrow experiences. In short, you get to live inside Poe’s The Masque of the Red Death, except without pesky Death wandering the halls ruining everyone’s fun.
Again, it’s not that McCain has it out for working people. He just doesn’t know — he can’t possibly know — what these people are experiencing. And if you don’t think there’s much of a problem, you’re not going to have the fire in your belly that you need to wake up each morning to help people.
That doesn’t mean of course that rich people can’t or don’t help working people — lots of them do. It just makes it harder to believe that they’ll make it a priority, particularly if there’s no evidence that they’ve ever tried in the past. And that’s what you have with McCain — a superrich person who has never made it a priority to help working people. Whatever his subjective motivations may be, all his economic policies help rich people and allocate them even more money. There’s no reason to think he’ll act any different as President. (Yes, many Democrats are rich, but many of them also don't put forth the effort and political capital necessary to really help the working poor -- maybe because they too lack a sense of urgency).
All that said, Obama’s attacks aren’t this intellectual — there’s a lot of gut-based resentment going on. But given the extreme and growing rates of inequality in this country, maybe a few pitchforks now and then aren’t the worst thing in the world.