Basically it's a mix between boomers not selling, and millennial's not wanting what they are selling (because what they are selling is shit). When we bought our home, we were looking at old (built in 1940's) starter homes in the 200k to 250k range and it was a nightmare. Anything that was great was out of our price range, and anything decent to 'ok' would be sold in the first 24 hours. Most of the stuff that wasn't selling was just straight garbage - stuff that would require a lot of work and money (50k minimum) to get moved into the 'decent' category.
There are plenty of new houses being built, but you have to go an hour or an hour and half outside the city. I have a family member and friend who went this route and they love it, but that obviously leads to long commutes and other downsides.
[1]: https://www.chicagotribune.com/real-estate/ct-re-millennial-...
"I can't afford to do the thing I want to do most."
"Then do something else."
If jobs in Toronto aren't paying enough to live there, move. Find a job making less money in a place where you can actually afford to live. I understand you may want the lifestyle afforded by being in a big city, but you're not owed that experience.
The answer is to flee these places, move on to greener pastures, these are barren.