These are actually some interesting questions that I never thought to ask (mostly because I had blocked Montreal's collapse from my memory! ). If Montreal keeps it up and takes out Carolina, I think the ensuing conference finals could have been one for the ages (if for no other reason than that it would have been the first time in a lot of people's lifetimes that the most storied of rivals have met in the playoffs).
Between an eighth-seeded Montreal team playing over their heads and a Toronto team coming off two series that had gone seven games apiece, I have to pick Montreal representing the East. Consensus seems to be that if Vancouver meets Colorado in the second round, the winner of that series takes out San Jose/St. Louis and goes to the finals. Given the storylines for Montreal/Toronto, I think they wouldn't have stood a chance against the Western Conference representatives.
Theodore was playing absolutely out of his head that season and in the playoffs before the game 4 meltdown where the team quit on their coach.