I found in Toronto, as a former Torontonian and born and raised near the city, that the biggest problem is that literally every conversation about the city leads to a Torontonian comparing the city too New York. Literally, always and only New York. A friend of mine actually just moved there, and as a point he only refers to Toronto as either little Chicago or cut-rate Chicago just to defy that norm and piss people off, and it works very well as intended.
On the flip side, I enjoy Calgary in that we look for the best ideas from around the world, work with them to see if they can work here, and then implement them if possible. The administration is looking at everything on the table and trying to pick the best available. It is starting to create a civic and built identity that is distinctly Calgarian, not coopted from anyone else.
This is not meant to be overly boostery, I don't find it to be. It's just what I've noticed watching the city develop quite rapidly and having also lived in Toronto, Ottawa, Vancouver, London (ON) and now here, all during my most formative years (17 - 26).