Depends on soooo many things. Just the division alone:
Ottawa: can they repeat? Kinda seemed like a genie in a bottle. Can Karlsson stay healthy? Does losing Methot hurt more than we assume? Anderson is going to be 37, can he continue to play at his current level?
Montreal: Can Drouin or Galchenyuk become a top-line(ish) center?
Can Price stay healthy?
Between Weber-Alzner, are they getting too old/slow on the blue line?
Boston:
How much more does Chara regress?
Can Marchand repeat?
Can Bergeron & Kreji stay healthy?
Can Backes fight of the inveitabile decline that comes with age.
Will McAvoy carry out his great playoff through an entire season?
Toronto:
Can their trio repeat their rookie performances???
Can they possibly stay as healthy?
Will their defense be any better? Or more of the same?
Tampa Bay:
Stamkos???
Can Vasilevski hold it down between the pipes as the full time #1?
Doesn't Dan Girardi make them worse???
Florida:
Will Huberdeau and Barkov stay healthy?
Can Ekblad rebound?
How much does losing goals from Smith Marchessault, Jagr (and even Jokinen) hurt?
Will Luongo hit a wall? And if so, can't Riemer step up?
Detroit:
Ehh... they're gonna be bad.
Personally:
I think they'll probably miss. But if no one in the division really takes it by storm, and 2-3 of the other teams have 2-3 of their big issues really hurt them, then I think we could have a chance if everything works out well.