When you're a fan for a contender, you get to experience both the thrill of victory AND the agony of defeat. Better? Sure. Always more enjoyable? Definitely not.
I'd much rather be a Bills fan this year than a Browns fan. Meaning I'd much rather be "in the mix" than not. That said, it's much more painful, as a fan, to almost get there and lose a close game than to not get anywhere close. So, for me, which would I rather be is different than which is more painful to endure. I'm sure Bills fans today are feeling a kind of pain that most Browns fans have never experienced, unless they recall those losses to DEN 35 years ago.
I'm a MIN fan, across the board. Don't really watch much hockey, but all of the other major sports. Basketball was my first love, and what I played growing up. During most of the Timberwolves' existence, I've been a fan, but they've never caused me near the heartache that the Vikings have. Pre-Garnett, the Wolves were terrible for several years, and it was no big deal. Then, they got close with KG, and it was devastating to watch them fall short. After that, post-Garnett, another period of mediocrity. It was what it was. I didn't lose any sleep over it. Last year was different, and I could feel the competitive juices start to flow again, in terms of wanting the Wolves to succeed. But, nothing like the Vikings, who have been close so many times.
Same with the Gophers. The Final Four with Bobby Jackson in 1997 is etched into my memory. Both for good and bad. Fun to watch, but hard to watch them come up short. Then erased from the record books, but that's another topic. Before that, an Elite 8 run with Willie Burton where they came up short against Georgia Tech's trio of Scott/Oliver/Anderson. Back when college basketball was as good as it's ever been. I can still see the missed three from the corner by Kevin Lynch that would have won that game. But, MIN hoops has more down years than good, it seems, so you get used to it. Nothing like the Vikings, who have caused me more lost sleep and gray hair than my kids have, probably.