Americans like presidents with whom they can empathize. They thought both Reagen and Clinton (two of the most popular presidents ever) were "like them," they thought G.W. Bush was the kind of guy you could drink a beer with (despite the fact that he's a tee-teetotaler).
Jill already wrote a great post about this, but I thought I would quickly follow-up.
First, despite the claims by McCain's staff that he owns "about 4" house, he actually owns 7 houses, in three states, worth 13 million dollars.
Second, this comes on the heels of John McCain's jokes about how rich equals an income of at least 5 million dollars. Of course, this was just a joke and came at the end of an answer which asked him to "define rich" and which he mostly answered by saying he didn't want to raise taxes (that wasn't the question John).
You can view a transcript of the event here time magazine.
This is another example of John McCain making jokes that belie his real world view. Hahaha, rich is 5 million dollars. Everyone knows he didn't mean that exactly (or do we?). His real answer? Probably in the million dollar range...who knows, he didn't answer the question.
Either way John McCain doesn't get it. The Obama campaign has a great ad below.