Can someone explain this to me at what point does one CHOOSE a house that expensive?

It's the rational behind it that I have trouble understanding. I'd say that most people that can clear the mortgage & property tax payments also have enough street smarts to spend the money on other things. What am I missing?

Say for this argument we skip foreign investors

Not sure I understand your question. You're curious as to why people buy a house that is what, a million dollars? You realize that $1M isn't much nowaday. I'm not downplaying it but even in sketchy areas small bungalows are $750k. Perhaps they want to move closer to work to lessen commute times and increase family time. Perhaps they want to move to a good area with good schools for their kids (kids are in school 14 years of their lives pre-secondary education). I'm saying this with the notion people have completed some sort of financial analysis and have deemed it financially viable.
Now if by saying "a house that expensive" you're referring to $2M, well its the same reason people were buying $1M homes 10 years ago.

The financially viable is the part I'm questioning.

Are they tapped out monthly, and carry forward debt each month or are they actually managing it?

Aka $120k income on 1.5M property drives old cars, and pretty much relies on cash

or

180k income, but everything is leased & revolves around credit & transferring balances & timing

Not sure if I'm explaining it right...

I don't choose to buy a million dollar home, but sought after hoods are the reason why it's so expensive. I want to live in Rhill, but I can't afford the house I want(detached,2car garage).

If risky was buying a house right now, I'm sure he would think "twice" about Markham. But chances are he would still buy it, even if it was double the price, right?

The question is why is Wayne still in Pickering

You are assuming everyone buying 1M+ is a first time home buyer.
Anyone with a home now that has substantial gains in equity can go and upgrade to a bigger house without a drastic increase in mortgage.

Cant afford unionville Leaside

Cant afford unionville

Cant afford unionville Leaside

One of my wife's old coworker had a place in Leaside, he was a Creative Director in one of the big ad firms. He's Filipino and out working his garden one day and one of his neighbours thinking he was the "help" asked him which landscaping company he worked for cause the lawn looked amazing.

I'd be triggered for sure!

I guess the difference between you and me is that we prioritize things different. You said you can't afford a detached 2 car, but could you afford a town, a semi, an old bungalow without a garage in R hill? I am positive you could, there still shit around 7-8, (R hill go train area, etc) It would be a HUGE downgrade for you though, but you could if that's what was important to you (living in R hill)

For me the house itself is the last on my priorities (I don't care, I can always knock it down and build), my goal first and foremost is a location that works (good commute, central, no scum, solid amenities, etc...all those are first before the house itself).

Different people want different things, if I had to buy now I probably would, but would have to get an even shittier/smaller house...but I wouldn't move to xyz suburb that I don't like just to get that "big house" that I don't need.

Port Union area is nice, it's under priced for what it is imo. Would move there personally (Go/highway/close to scum but far away enough, water, parks, etc)

Where did your parents move to?

Nice, I think we drove there before anything was built. Is it a detached/2car? Swap houses with them

$4800

So you gonna be coy or are you gong to post up the hardly shocking assessment details?

https://www.realtor.ca/Residential/Single-Family/17027349/28-WAVERLEY-RD-Toronto-Ontario-M4L3T1-The-Beaches

saw this place this weekend while roaming around...figured it'd be like 1.2 to 1.5 mil...lol, nope.

more. damn.

House a few blocks away just sold for 75k over asking, lol Barrie.

poverty appreciation