So I'm not trying to sound negative but a key thing to remember about Toronto is that it's still a city that fears being in the big league (and by that I mean most people who have any decision-making power).
Look at what Canadian developers propose for Australia, the UK and the US and even Calgary vs. what they propose for Toronto (for office buildings). Calgary definitely has better looking new office skyscrapers than Toronto's (again, new)....
Look at how badly planned 10 Dundas East is and how silly the whole Trump debacle is - yes, it may be that planning did not know these buildings would turn out like this but still, I don't recall seeing such obviously ugly-looking buildings in other key cities' downtowns.
Toronto will continue to have far too many ubiquitous boxy towers that will have a large grey component to them, silly restrictions of all kinds which will plague our city, and despite minor improvements, the city will have a somewhat shabby public realm. And transit will always be an issue in our lifetimes because even if all the necessary expansions are made, they will take far too long for most of us to truly benefit from them. How many years will it take for the spadina extension....nine years for six stations?
In a way, Toronto is a stunted city (compared to its potential). Yes, I know, I've said negative things in a thread about the Mirvish towers but sometimes one can't help it.....
And in case if someone is wondering why so many people to choose to live in Toronto, it's because people still like this city inspite its shortcomings...it's just that when you're passionate about you city (like I am), you can't but help be frustrated at all things that are so obviously wrong...