Good post- and it's all preference. I watch and follow a team to enjoy the entire season. Rings for me don't matter that much- if they have a winning season and just make it to the playoffs... I probably had very fun and entertaining 160 games.
You can buy, build, manage, coach... a winning season. Winning a World Series takes a lot of luck and timing on top of that. So to me I don't get too excited about not winning it all.. in any sport. But choosing a losing season is tough to swallow.
If I could choose:
A. 5 winning seasons and making the playoffs twice, but no world series win, or
B. 1 World Series win and 4 losing, basement seasons...
I'm picking A every time. I'm probably in the minority with that- but that would be my preference.