Earlier quoted context omitted.
$300k (household) isn't upper-middle, before the term became diluted to mean "middle, but with a little left over every month"—the upper-middle of Fussell's Class and The Official Preppy Handbook - Good private school for a kid or two (guess what one of the bribes to Thomas was...). Not gonna get away with much less than $25k/yr/kid, there, and it goes up from there. - Long vacations expensive places a couple times a…
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 e…
The median condo is not particularly great - and it goes for ~$660k in most of the nicer neighborhoods.
The median house is well over $800k in the nicer neighborhoods.
And, again, Chicago is one of the most affordable cities in the US.