It has a lot to do with how you weight playoff appearances and World Series wins against never being bad.
Like the Yankees right now are constantly a decent team, but haven't won anything recently. Same with the Jays.
On the other hand, teams like the Astros, Red Sox and more recently the Orioles have gone through stretches where they were absolutely terrible, but have also had some major postseason success.
I lived through the 1992-1993 World Series wins. I can honestly say that it is absolutely worth living through some terrible seasons in order to feel that kind of joy. Others' opinions might vary.