It seems that per sf house prices haven’t gone up that much. We romanticize the idea of older generations being able up afford a home, but those houses were a lot smaller than they are today, the average size I think was around 1500 sf, and a family of 5 lived there. Cities were also not as livable as they are today. Take for example NYC in the 1970s and 80s, where a young photographer could afford an apartment in Manhattan, with the caveat that the area was riddled with crime. Then there are the city ordinances that discourage multi family housing, so if you are a builder and you need to decide whether spend years fighting in court vs going to the suburbs and build large homes, that’s a very easy decision to make. The current housing deficit sits around 3-4 million homes.

Per sf comparisons blatantly ignore the bonkers increases in land prices. Good luck finding a 1500 sf house, let alone one with a backyard that hasn't completely outpaced inflation.