Now that VGK has suffered the inevitable Fleury playoff gaffe (I was watching with my son the other night - the first thing out of his mouth after the puck-handling Gaffe was "you called it"), I think they'll recover to beat the Habs. There's just too much of a disparity in talent for the Habs to win 4.
I think many at the league HQ wouldn't mind seeing a Habs/Isles finals. However, one of the bad side effects, besides re-legitimizing DPE hockey, is that they'll see no need to fix the cap rules to avoid TB-like circumvention.