I don't know anything about the broader argument here. I responded to a comment that said that $300k/yr would only get you a small place in one of the nicer neighborhoods in Chicago. That's categorically false. Mortgage calculators are premised on other expenses scaling with your housing cost, and capture the other bulletpoints ("country club membership", really?).

Someone with a $300k/yr income will end up with an extraordinarily nice home, by any standards, in Chicago.