Yes, actually, I do think, solely in terms of economic mobility and wealth accumulation, that the "greatest generation" had it easier.
Here's an interesting study on generation elasticity (the chances that you'll remain in your parents' economic bracket, essentially) that helps make that point, although it's not clear cut. But the gist is that economic mobility snapped back to depression-era levels around 1980. There's plenty to chew on in that data for both sides of our debate, but it makes a compelling case that American meritocracy has gone off the rails.
More importantly, that generation didn't require as much education to establish long-term employment, gainful employment was readily available after the war, and unionization, pensions, and social programs helped sustain that generation through the golden years.
I'm not a millennial (I'm turning 40 soon), but I certainly see that they're getting screwed, even more than my generation. Moral failing didn't cause this.
Which came first, the chicken or the nest egg?
Check this out.
The problem isn't that people are having kids too soon -- it's that they can't get enough economic footing to sustain families. I would argue that economic pressure as well as changing social norms are behind that unwed birth stat.
Regardless, the answer isn't just "work harder and get more schooling." We need to lower economic barriers, cheaper education, and we're probably going to need more robust social programs as my generation and those below me age. It's time to raise taxes on the wealthy.