I was at Game 2 of the 2005 World Series (for free though, grandfather got me tickets), and it was awesome enough that I could easily justify spending $1000 on a ticket for another one, and I'm not Mr. Moneybags or anything, and I'm almost always on the "staying home and watching the game on TV is better than being there live" side.
EDIT: On second thought, I'm biased because that game was all kinds of awesome. If I spent $1000 only to have the Sox put up a stinker I'd be full of regret. Hmmm...