Huge productivity growth doesn't seem to have translated into commensurate wage growth. Meanwhile housing, higher education, and health care are increasingly unaffordable, as you note, and credentialism makes higher education a requirement for more jobs.

I think you're on target about the discouraging aspects of being visibly worse off than your parents' generation, and I think that millennials have that problem as well.

The situation is likely to get worse as AI-fueled productivity increases are unlikely to improve wages either.