i'll try my best to make this post civil to avoid offending any visiting fans who may be reading this; (and to be different I'll answer the direct question at the end of the post)
so who would I be cheering for if the other canadian teams were in the playoffs?
I've never cheered for the habs in a playoff game. I think the only scenario I could see myself realistically doing that is if a habs team I didnt mind (such as the 2008-2009 version in which Carbo coached) played an Ottawa team I extra despised.
Ottawa I generally cheer against but I can be persuaded to tolerate them at times. Truth be told I actually like the current version of the team and the way Paul Maclean runs them. I generally cheer against the non-hockey markets in the playoffs, so I did have trouble deciding whom I wanted to lose less between Ottawa and Anaheim. I finally decided since I disliked Alfie, Spezza, Heatley, and Neil and the fact that we'd never hear the end of it if the sens won a cup that I'd cheer for the ducks. After Alfredssons puck shooting gaffe, I was firmly on the ducks bandwagon.
As someone mentioned above, the only issue we seemed to have had with the Oiler fans was around 2001 when they got decent again (not sure why they hated us so much at the time, was it the Cujo factor?) I definitely cheered for them against the Hurricanes in 2006.
Winnipeg is a team I'd probably cheer for against any other at this point. While they are still fairly popular, the fan base that attends games has become adept at trolling the other team (this is not a criticism, they are clearly trying to be the 7th man), I can envision them drawing hate.
Vancouver I dont have an issue with the franchise or fans, if pretty much any version of their team prior to 2009 made the finals against an american team, I'd likely cheer for them. But I could not bring myself to cheer for that team of rats and divers to win in 2011, knowing how horrible it would have been for hockey if a team won the cup playing that way. I actually think if the Canucks met the Sens in the finals this year, I would cheer for Ottawa.
now the issue at hand; Calgary has always been my 2nd favourite team (although Winnipeg may be now); I cheered for them every step of the way and the following they had was astounding. That year was one of the rare playoffs where the finalists were more memorable down the road than the champs (though 2011 may shape out the same way). Andy winning was a nice silver lining but no where close enough to be glad the lightning won.