IMO, there's another part of the problem OAM referenced in addition to the skills-track y'all are talking about. Financial literacy. It's true that it's harder right now to achieve the baseline middle class standard of living we think of as "normal," but the problem has also been exacerbated by a total lack of knowledge of what a plan looks like, how to implement it, how to budget for it, and then the discipline to stick with it (that last part maybe doesn't fall under financial literacy).
Recently my youngest stepson has complained a lot about what the world, Boomers, Xers, politicians, etc. have done to him and how hard it is now to make ends meet. I got tired of it and just the other day sat down with he and his gf and crunched the numbers on what they make right now, what they stand to make with potential entry level jobs in their fields once they get them, and what realistic bills and expenses look like in our little corner of the country. Lined it all out for them, including savings, all the way through to hitting retirement goals, both individually and a scenario where they're married and have two incomes. It does seem harder than when I was starting out, but still very doable. I told him the worst part at the moment is he won't have the "luxury" he's used to here while we pay all his bills, for a while, anyway.
He still grumbles about it, but now with some awareness that he doesn't really have very good points. I'd like to tell him we'd be doing better than we're doing right now if he'd quit taking his sweet time through college, seemingly unaware I don't feel like paying tuition forever, or of the boon he's being handed by getting out without any debt/student loans. But I don't.