I think often about the shirtsleeves to shirtsleeves or variants as that kind of thing has happened in my family, both sides, multiple times. My mother experienced all that in one generation. Her parents were not well off, but her father came from a respected established family. Her mother from a farm family with many children. So while my mother did not grow up with the finer things in life, she knew relatives,ancestors like that. Her grandmother paid for her to go to college. My father was a self-made man, first generation American. His grandfather was someone who was considered very smart and also pulled himself up by his bootstraps with thriving business, but his unexpected death, and his son's illness and then death meant everything they built was lost. So, father moved to the US and started all over and build his way up to creating a financially successful life. My mother's way of dealing? Though she didn't spend a lot on herself (didn't know how) she had us kids especially her daughters enrolled in summer art classes, camps, horseback riding lessons, all the things she wished she could have done as a child but didn't have an opportunity to. We were also never given any real world lessons on money, or limitations where we would apply for college. My father had a major business setback while I was in college, parents divorced. So they ended up losing everything. My father did it again, building up from nothing, having a successful business that provided jobs for the rest of my siblings, but then lost all that in last recession. Neither have anything for retirement, other than social security.
Anyways one of the things that I wanted to point out, it is not necessarily the younger generation's "fault" they are not as "hungry" at making money and being successful, because consciously or not, the parents may have compensated for their own deprivations with their kids, and maybe didn't want their children to worry or be concerned about money, which is a luxury for only the extremely wealthy.
