I've been about 20-30 times as well, and I have mixed feelings. The Colosseum in Rome has a significant amount of history, but no teams still play there. The history and prestige is important, but if a new stadium means cheaper seats and better views for those of us who can't afford box seats, and more revenue to make the team better, it absolutely must be done. The past is important, but shouldn't the present be the first priority?
I bought tickets to six games last year, and will probably be around that number for 2012 as well. I'm slim enough to enjoy the seats comfortably, and I can enjoy Fenway for what it is. But if there is a time when it just doesn't make sense to stay there, it won't make sense to stay there.