I would cheer for the Leafs over the Jets without a doubt, but it would be painful. I live in Winnipeg but was unfortuneate enough to be too young to remember the old Jets, fell in love with the Leafs at a young age. Now that the Jets are back I cheer for them out of hometown pride but the Leafs are my #1 team always and forever.
I live in Buffalo but am a Kings fan. I go to a lot of Sabres games and pull for them but when they play the Kings it's all feelings for the Sabres go away. I'm 18 so I began to be a Kings fan the year before the lockout (might have been 9-10? I don't remember) but since I've gotten older I'm pretty much solely a Kings fan now and pull for the Sabres because they're my hometown team. But yeah, I'd pick Kings over Buffalo 10/10 times. I stay up until 1030 every game night and watch start to finish to see the Kings play. So I don't think it's a big deal I cheer for the Sabres against a lot of teams.
I like a lot of other teams, often due to the players they're currently rostering, but sometimes due to heritage of the team as well. For example, I like Detroit a lot and always have.
If the Rangers met Detroit in the finals, it would be a no brainer to root for the Rangers and there would also be a chance that my liking for Detroit would be decreased for a while after the series due to bad blood.
In other words, having two or more teams is okay, but everyone has a main team. The Rangers are mine and there's no scenario on earth where I would root against them in any game or series.
Canucks used to be one of my favorite teams. Admittedly, I started to dislike them more before that series started, but it just ramped up to full on hatred in that series, and it hasn't really died down at all. It's amazing what one playoff series series can do to completely change your opinion on any team.
even if you can consider yourself a fan of two teams (which i doubt), one will prevail. i will never have a dilemma if Oilers (who i'm a fan of) meet Predators (who i more or less follow) at some stage in playoffs.
Pens and Wings were my two favorites when I was a kid but I've sort of lost interest in the Wings over the years. I rooted for Pittsburgh both years they faced each other. There are a few teams that I like, have players I like, that I will root for when they aren't playing the Pens, but there's not going to be anyone that I would want to see beat the Pens in the SCF. The Pens could win the cup 10 years straight and then go up against CBJ (my hometown team) and I still would root for the Pens.