I know a lot of professional people in my generation, and I know of only a few that have anything like what you describe.
One managed to land a six-figure job in Kentucky, one of the lowest cost of living places that was largely passed over by the housing bubble. The major reason he's well-off is that his house was affordable and he went to a lower priced university and didn't need much in the way of student loans. He lives in a ~2000 sq. ft. house that cost about $175k when he bought it. Where I live that house would be $400k, and it's not even a major city. Median incomes where I live are no higher.
Another had a liquidity event. Another owns a hugely successful online company.
The vast majority -- vast majority -- of the peers I know do not live anything like what you describe. These are not slackers either. These are hard working, highly educated professionals. Many of them routinely pull 60 hour work weeks doing things like computer programming, business, marketing, and high-end interior design for wealthy clients.
I honestly have no idea how people making the median family income can live, unless they live in horrible neighborhoods or in the middle of nowhere.
I didn't say "Earth to Planet Trust Fund" just to be snarky. There is a culture of people who grew up with wealthy parents, had mostly paid for rides to places like MIT, and earn six figures, and really do have kind of a "why do they not eat cake?" view on this stuff. In my experience they're not bad people. They're just insulated and ignorant. They have absolutely no idea what they're talking about if they think their situation is anywhere near normal.
Again, public enemy #1 here is the housing bubble, which from an income/value ratio point of view is still in effect. #2 is the cost of college. The former has increased somewhat in quality since the previous generation, though not enough to justify a quadrupling (or more) in cost. The latter hasn't increased much in quality at all, but the cost has skyrocketed.