I think I prefer Calgary's to Vancouver's. There's just more meat in the more common angles I get to see. Not that there's anything wrong with glass condos - I'd take every single fucking one ye've got here if I could.
Toronto's is just awesome. It's the only one in Canada where you can take certain angles, crop off suburbia in the distance, and imagine a truly overwhelmingly large city. And even its glass condos have a certain expensive quality. It's the difference between having a proper wooden blind or a flag in your window.
And Montreal's is just lovely. There are a couple of buildings that are so hideous they kind of ruin it for me in skyline views, but angles where you can't see them as the focus (so basically anything not taken from Mount Royal), and it's just grand. Love it.
Among the smaller cities, Regina stands out as aesthetically pleasing to me. And Halifax stands out as a mish-mash of ugly and beautiful buildings that works. There's just something engaging about a shot like this:
Source
(Hali87 gave me that picture for
a thread on Boston I did; I wanted to show some of HFX proper since my photos from my trip were just of the airport).