I suspect I may get some blow back for this, but I don't specifically need the team to win the Cup, in order for me to enjoy watching the team and/or to feel good about their season.
If the Avs top 100 regular season points, get into round 2 and play a competitive round 2 series - that probably makes them a top 6 team in the league, and I'll probably be OK with that result (particularly if they do it while continuing to develop young players).
Kind of like either Toronto or Winnipeg this season. Very good regular season(s), won a playoff round, were competitive in the 2nd round. No Stanley Cup there, but that's a damn solid season, all in all.
If I become so binary that I enjoy the game and/or the team ONLY if they win the Stanley Cup, I'm not sure that's worth it.