This is part of the problem, Toronto specifically has to pay for two highways that are almost entirely used by people who don't pay for them. Building that middle density housing would fix a lot, but we'd actually still be in a difficult financial position, because municipalities here are so limited in how they can generate income. The province can override any decision a municipality makes whenever they want, and that neede to change.

By providing all that shit for free, we've basically been subsidising lifestyles that are otherwise wasteful. And then we added low-density zoning on top of it, so here we are.

I'm not on the private roadways "train" (lol), but I think they should be self-funded by a hypothecated tax, or user fee depending on how you want to look at it. If we did that, public transit would probably grow itself.