None of what you are saying is supportable by any data or statistics.
The boomers had everything worse. When they were born, something like two thirds of them had indoor plumbing. And a third of them did not.
My parents, my grandparents, they grew up the same way everybody else did back then. They worked on a farm from the age of like 5 doing manual labor.
When you are talking about your parents, you are talking about the luckiest people in the country. Nobody got a pension back then. Maybe if you worked for IBM, but that was not the norm.
What you are saying, "every plausible life-path got downgraded a couple notches since then" is completely false. Every plausible life-path has been upgraded since then, the things you are saying just aren't true.
Yeah, I know, I’ve hand-pumped water at the well my dad used growing up. The ‘40s and ‘50s were rough for a lot of families—but their kids basically just had to not constantly fuck up for multiple decades to be on track for at least moderate success.
I think it’s why a lot of that generation (my parents included) assume anyone who’s not doing at least decent is basically not trying at all, or is astonishingly useless. For their relatives who didn’t climb out of poverty with the rest of the wave, that’s mostly true.
(YMMV for minorities over the same time span, of course—racist FHA policy and other measures meant e.g. black folks didn’t get such an easy on-ramp to the postwar-success highway, to put it mildly)
To take it to an extreme to illustrate why this may matter, if one town gets abandoned and the houses all sell for $1 to a single family, while all the former residents move to another similar-sized town that sees prices more than double… you’d be best off ignoring or down-weighting the effect of those $1 houses if you’re trying to figure out how the housing market is looking to most people.
Though it’s possible the figures used for the analysis already account for that kind of thing, in some fashion. Are they actual sale prices, or asking prices? Do they only count sales to someone who’s intending to use the dwelling as a primary residence, or all sales? There’s a lot of room for the median experienced house price for a person just trying to buy a place to live to differ from the median on-paper, depending on how it’s handled.