It means something to me as a fan. It means I am watching a team that is competitive, they're fighting for something, and not just mailing it in or playing the spoiler.
The 100 years thing doesn't bother me. I'm not that old.
Well, yea, it helps that the team isn't a mess and is in the cellar each year. Regardless of your age or mine, 100 years without a World Series is pretty bad. I mean, geez. That's a CENTURY without ONE championship. Divison titles and competitiveness are nice, but come on, without a World Series, you're still known as the team that can't get it done.
A lot of Cubs fans are from Chicago, are born and raised Cubs fans, whatever. But there's also a lot of Cubs fans that are fans for one reason or another - usually because it's trendy.