Some misconceptions here. The good old days that still existed in the ‘80s and early ‘90s were kinda still there, but the signs of economic retreat were there too. We were offshoring a lot of manufacturing, bankruptcies were tools to get rid of pensions and union strength, and then everything Reagan did to fuck us that just wasn’t apparent yet. They weren’t the good old days that the Boomers had, but they were far better than today.
You could still rent a place for a few hundred bucks on a single job, community college was ~$50/semester not including textbooks. A cheap house in a not so great area was ~$100k, often a lot less. People didn’t use credit cards the way they do now so debt wasn’t as common, it was harder to spend money you didn’t have. You could still claw your way ahead or at least tread water.
2000 was a turning point. The dot com bust, 9/11, offshoring of even more jobs in tech, multiple recessions, endless war, and corporations running out of ideas other than finding ways to extract more and more from the consumer while offering less in return. Every generation since has had to deal with more things being put out of reach.

