It all depends what your personal perspective and experience is. As a die hard Leaf fan who lived in Montreal for a while in the late 2000s, thinking about how much they despise our team makes my blood boil. It definitely opened up my eyes to the rivalry (I was more of an Ottawa hater before, as we played them many times in the playoffs during my childhood) and made me a life-long Hab hater. If you only go to Montreal for short vacations, I understand that you won't pick up on that vibe.
It's beyond me why any Leaf fan would wan to give their fan base those bragging rights of winning another Cup. I get that the whole concept of cheering for grown man in uniforms pushing a puck over the goal line is silly. However, if you chose to partake in that and support one team in particular, why would you want the enemy team to win?
So yea, I'll take the astroid option as well rather than them winning the Cup.