Your sneaking suspicion is correct for baby boomers and gen X: http://www.pewtrusts.org/en/about/news-room/press-releases/2.... "Gen Xers have less wealth and six times more debt than their parents did at the same age," despite having higher salaries.

I think you're right to be concerned. Not being able to strike out on your own delays family formation, which leads to some attrition of people who never have children for financial reasons. This decreases the birthrate and then on top of the working generation supporting members within its own cohort, they also have to support an older generation of retirees with an ever rising dependency ratio. It's a negative feedback loop that countries like Japan, Germany, and Italy are stuck in.

Both the education and housing problems can be solved. Education can be automated and amateurized using technology, and more housing can be built. Both of these would do a lot to decrease youth debt loads. Medical price inflation is the tougher problem but is less pressing for young people. Eventually we will be old though and then it will hit like a ton of bricks for those unlucky enough to have not accumulated wealth.