Well now that we've had some time to review these teams:
Calgary or Winnipeg have the best chance of being a Canadian team to win, because I don't see the Leafs getting past Boston and certainly not Tampa in the East. The Flames and Jets at least have a decent chance of making it the final, and then depending on injuries and wear & tear, whatever happens happens.
Until a Canadian team finally wins the Cup again, I will always assume they won't do it. The odds