Clif at Sadly, No! explains it all:
Look, I actually think that of all the attacks on McCain, the one that he doesn't use email is perhaps the weakest. I prefer things like, he wants to raise taxes on the 60% of Americans whose health care is provided by their employers or that he doesn't actually know who we're fighting in Iraq or that his campaign has deteriorated into a series of outright lies and schoolyard bullying.
- The reason that McCain wears $520 Ferragamo loafers is because he can't tie his shoes.
- The reason that his Senate office tried to cover-up Cindy McCain's drug addiction problem was because, if she went into treatment, there wouldn’t be anyone around to comb his hair.
- The reason that McCain campaign aides took away his unlimited cell phone privileges is because he dialed too many wrong numbers on the cell phone keyboard
In fact, I think Obama has sadly fallen for the right's Indignation Defense--the art of taking every single thing a liberal says and being offended by it as a personal attack. (We must remember, of course, that liberals are not allowed to be offended, or so says one of Charlie Sykes's 50 Rules.) The lipstick thing, the houses thing, and even the email thing are not personal attacks (McCain's lack of interest in the technology that drives contemporary American commerce and society is a disturbing artifact of his being out of touch, not of his being a POW). But the right has perfected the swoon and faint.
Imagine, for example, a group of liberals selling boxes of John McCain rice ("McCain's answer to every question is 'For five years I ate nothing but rice--as a POW!' "), decorated with pictures of a whiter-than-white elderly McCain coming down the stairs of his wife's private jet in front of one of their estates, at a conference attended by Hillary Clinton and Harry Reid. We wouldn't hear the end of it; the bloggers would post a hundred times a day, the radio squawkers would devote weeks of programming to it, FOX News would ask why liberals hate America and if the next step was ritual sacrifice of goats to Baal.
Of course, no such thing happened; instead, it was conservatives selling Barack Obama waffle mix, full of racist imagery and exploiting the stereotypes the right's been spreading all year. Democrats, unfortunately, have not mastered the Indignation Defense, and so such things will go on and on and on. Which leaves Obama in a quandary: Republicans and the media won't talk about the issues and don't care when Obama does, but Obama can't say anything that generates press except things the right can swoon and faint over.
(Similar situation: Remember the right's swooning and fainting when a conservative Wisconsin blogger was threatened by a petty, power-abusing mayor? Think they give a crap that Governor Palin did the same thing?)
There's no good way to win this, and I don't have an answer. The best I can do, I guess, is keep pointing out how stupid the right looks when it mounts the Indignation Defense.