I'd love if Toronto had more 5-story apartment buildings. I don't want to live in a giant condo having to take long elevators and pay expensive condo fees. But I hear it's nearly impossible to get regulatory approval to have those built here, it's either big high rise condos or nothing.

Montreal's plateau has a nice arrangement. Plenty of 3-5 story houses built in the 1950-60s broken up into multiple apartments making it the highest density area in Canada. Rent is super cheap ($450/m got me a large bachelor unit a few years back that would have been around >$1000 in Toronto).

The problem is retrofitting density.

Toronto is trying to quickly deal with it's increase in demand for housing. It can either try to build 1000 5-story buildings, or 100 50-story buildings. Which do you think is easier to do (financially, politically, everything else...).

It's all well and good to say "neighbourhoods with thousands of medium density buildings would be better", but we have to deal with what we currently have.

Now, long term I'm 100% in agreement with you. We need to modify regulations to say that new things must be of a certain density minimum, to gradually increase density everywhere. Consider taxing property in part based on density maybe? But in the short-term, towers have to go up or no one will be able to afford to live here next year.

As for comparing Montreal prices to Toronto prices: again that goes back to supply and demand. If Montreal had the immigration rates Toronto does (5,000 new people per month is the estimate I heard, and that's just from abroad), you wouldn't have cheap rentals. If Toronto hadn't worked hard to build towers, prices would look like the Bay Area.

One problem with mid-rise apartment buildings in North America is that they're of wood/plywood. It's one thing to live in a plywood SFH by yourself, but quality of life decreases (at least for me) rapidly in a mid-rise arrangement due to noise.

Anything over 7-8 stories has to be concrete, which makes for a much better condo experience.

It's not too hard to build a wood-framed condo that is noise-resistant. You just need separate frames for each condo. That adds to the cost, so it's not typically done.

Yes, much of Europe provides an adequate supply of housing. It's not done via massive skyscrapers, but lots of 2/3/4 story buildings that make effective use of space.

"Adequate" is being nice

In the end, skyscrapers, while having problems, allow for bigger units (on average) in comparison to Europe

Adequate in Western Europe is adequate in the Bay Area or NYC. We're not talking about Hong Kong or Tokyo here.

The unsurprising problem is that the bay area isn't one of the European cities that grew dense and people therefore like to take as an example. It's very like that if the bay area want to grow significantly it has to do so with a business district on mostly vacant land.