BG, although I, personally, did not have the same home buying experiences you mentioned with regard to many Boomers, I do agree with your analysis of the changing dynamics at play.
When I mentioned that it seems the home-buying experience is becoming more challening today, I was actually referring to the costs involved, etc., (especially if you actually want to own the property),compared to when I was purchasing the bulk of our properties.
I know everyone has their preferences, but much as UCGal mentioned, most of my family, and my wife’s family has always been drawn to NCC (others just coastal) for climate, schools, easy commutes, etc., long before that lifestyle became so in vogue with the current crop of buyers. NCC living is not really a new way of life as many seem to believe.
At any rate, regardless of preferences, everyone should try to enjoy life, because, as you also said, it is short, and there is much to do!