Let's crowd source this so we can actually contextualize it a bit. Feel free to critique as I haven't spend time in most of these cities, but I'm a bit of a geography/weather buff. Obviously a lot boils down to personal preferences:
So there are about 10 teams with good-great weather, and 2 that are pretty terrible.
The other 20 vary wildly, but overall the differences probably aren't super significant. That said, Calgary is certainly in the bottom half, but there are things to dislike about the weather in a lot of the cities.