I guess it depends on what you want out of the situation. I enjoy watching hockey (usually just the Leafs, because I enjoy a number of other things that I spend time on). I enjoy it a little more if the Leafs are doing well. If they happen to win a Championship, great. I'd love that to happen. If they suck some years, I put it behind me and move on.
Overall, it just doesn't seem to make a lot of sense to get worked up over some that is so far out of my control.
LOL..."some years"
They've sucked for pretty much 10 straight years now.