I don't think the lives of Cub fans would be much different had they won just 1 world series. I think the Red Sox are in a different point because they got a couple.
A single championship from nearly 10 years ago is a faint and fleeting memory for the average fan. I grew up a Buccaneers fan. The 02 NFL championship is so far in the rear view mirror that I don't really ever think about it other than when NFL network has it on America's game. 10 years later, it didn't change Tampa bay fans lives. it was awesome when it happened and then it all came crashing down.
Do Pistons fans sit around and relish that 04(?) championship team, or do they better remember the late 80's era that not only won a couple but were a really good team for a long time.