Midtown Urbanist
Superstar
Its fairly evident walking through the neighbourhood that:As someone who has interacted with this neighbourhood for nearly thirty years, I can attempt a short answer: In large part, Boomer U of T faculty who bought in at the right time, and the right place.
A) despite it being an extremely highly walkable neighbourhood, you will hardly see anyone walking if you venture north of Bloor.
B) if you pay attention to all the daycare facilities and schools in the area, the kids who attend these facilities are being driven to and from Wychwood/Forest Hill and possibly beyond by their parents. They are not locals.
A complete neighbourhood it is not. Jane Jacobs may have famously coined the Annex as such, and it likely was at one point in time (way before my time), but today it is the home of Margaret Atwood types, NIMBY and all.
The most egregious part of this to me is how the neighbourhood is protected by Heritage Conservation Districts to prevent any sort of change in the neighbourhood, despite it having an extremely generous 5 subway stations within it.
City Planning is not helping either, by pushing design guideline policies along the Bloor corridor, the one area of the Annex that is allowed to see intensification (sorta, everything is still being appealed to the OMB and now LPAT), and on Dupont. The TOCore initiative will also be restrictive.
It pains me to see such a well serviced area of the city so close to the downtown core be essentially frozen in time.