Being a fan from 1984 - that was 13 seasons (and 1995 Final) of frustration, and near misses for me until Detroit won the Cup in '97.
I realize that Detroit hasn't been good literally forever. I'm suggesting that this upcoming season, for instance, will probably be more interesting for me than the 1999 or 2000 seasons. Even though these were heyday years of the Wings "dynasty".
I like the question marks surrounding an upcoming season. Going into it with Cup or bust on your mind is fine (especially if you haven't won in a long time), but it's a little less interesting when you've seen a ton of them.
I love the competition for spots, the youth movement, the goalie debate, the new coach, the emerging stars. All those story lines are more interesting to me than anything we were talking about heading into the 2010 season (for instance).