I understand most of your argument however I'm not buying into the baby boomers thing. Most people with enough disposable income to buy high end cards are little bit older than you or I, but I don't think it falls into a category of generation, other then post-war collecting nostalgia.
19th century, for example, can't possibly carry some connection to any current collectors childhood yet prices are very strong. Since coming to this board, I've learned that some collectors don't even like modern baseball.
So it seems being a fan of baseball isn't even a prerequisite to collecting baseball cards.
The people you describe, being buried in debt in the future, already exist. Yet you still can't get an E107 for a T206 price. There'll always be one guy with more money than the next guy, and he will be the one who has the better cards. No big deal.