For Vancouver's geography to be a legitimate concern, we would have needed to maximize what we could do with the existing land, and it's very, very far from that.

I would argue the latter 2 arguments have some bearing, but imo it's more about cheap capital coming in from many directions including locally for so long in combination with artificially choked and inflated development processes for decades. For example, there's a parking lot with an old grocery store sitting there at the busiest transit hub in the U.S and Canada. The proposal to redevelop the site has been repeatedly stalled every year for what is now 6-7 years, meanwhile only the most meager development projects have gone forward in the same neighborhood. That said, because of the other reasons, as soon as it hypothetically went up, all of the units would be purchased by speculators because they'd be wildly out of reach for any regular person anyway, due to decades of the other crap.

I went to an open house yesterday for a modest one bedroom with no interesting view or extravagant features, listed at $750k. When I remarked that the cost of the mortgage alone would be a multiple of 2.5 - 3x our current all-in expenses, he simply suggested that in 5 years I can just move out and hang on to it, renting it out to someone and keeping another unit off the market.

The geography wouldn't be a problem if maximizing use of the land was done. You point out the choked development processes, but other open geography locales would still have those bureaucratic problems in cases and yet just sprawl out elsewhere, reducing prices. Take a look at Houston, Dallas Fort-Worth, Calgary, Edmonton metros. There is a reason those metros have retained low housing prices while they have grown so much. They are able to grow out. Vancouver and SF are much more limited in their ability to grow out Single Family Homes when high-rise development is choked. That's why the geography issue does have bearing.

Meh, the greater Vancouver area including the adjacent cities have sprawled as far as they can and continue to do so; there's actually quite a lot of development happening in some of those suburbs, and they can be just lovely. The other cities you mention—if they've kept prices low—they're embracing an obviously horrible development pattern that only works because they have oil money and it hasn't collapsed yet. Smaller, less-resource-rich cities like Winnipeg have tried the same thing and literally couldn't afford to maintain their own infrastructure if all they had to pay for was road maintenance. Yes, you can buy a $400k condo there, but as they come to terms with the rate they're reaching insolvency, they'll need to find a way to very quickly turn what are already near the highest property taxes in the country, into 2-3x that number.

The geography is a constraint, the problem is failure to embrace the constraint in any sensible way. Prairie cities would be more economically productive and less horrible in my opinion if they halted outward expansion decades ago and just figured out how to adapt correctly.