The "illusion of things going well" is rapidly fading. Many of my peers (born 1987)are struggling mightily to find secure and rewarding (financially as well as mentally) employment -- not to mention their massive student loans. I was fortunate enough to find a path where I didn't require a large student loan hanging over my head -- but it's hard to ignore all the other factors that are pinching people (low wages, rising costs for food, extraordinarily high housing costs).
Reading the article, and trying to look forward 10/20/50 years, it's hard to make heads or tails of what may happen. The article suggests that older generations are generally 'on-track', due to the fact that they're the predominant home-owners -- but the Great Recession was caused by a collapse of this very sector, which has apparently 'recovered'. I think in this sense, recovered is code for "has begun to reach unsustainable highs again".
It seems to me that unless something changes significantly (affordable housing and right-to-housing laws), these 'older generations' will be left sitting on their extremely over-valued properties that nobody can afford to buy from them until things inevitably implode. As far as I can tell, if nobody can afford to purchase what you're trying to sell, it's not worth what you think.
The last time masses of people tried to get into the housing market -- it collapsed. It strikes me as a "damned if you do, damned if you don't" scenario. Maybe the next Great Recession will actually be more of a Great Equalizer. I doubt it's far away, either.