So, if anyone is a fan of winning teams, what does it feel like?
Well, being from New England I have seen both ends. As Jaffa Cake states, it is better to keep following one set of teams all the way from the lows to the highs rather than keep chasing after different teams just because they are good.
I remember the Patriots getting crushed in SuperBowl XX by the Bears then a string of bad teams putting up 2-14 and 1-15 seasons. When they won SB XXXVI I couldn't believe a Boston team not named the Celtics had just won a championship. (I was 3 and 5 when the Bruins won their last two Stanley Cups, so I don't remember them.)
I remember Red Sox teams as far back as '78 when they lost a one game playoff to the Yankees and also remember them losing the World Series in '86 to the Mets (the same year as the @#$%!@# SuperBowl XX loss) after jumping out to a 2-0 lead. When they won in '04, especially after handing the Yankees the only playoff collapse in Major League history after leading a series 3-0, I was even more in disbelief.
I remember the Bruins losing in the Stanley Cup finals in '88 and '90... well this one is still ongoing.
Over the last ten years or so things have looked good: three SuperBowl wins, two World Series wins, one NBA championship and four teams playing well enough to at least have a shot in the near future. But it certainly wasn't always like that here.