I'm sure it does happen but if 'every' Boomer has that life then that might have more to do with where you are or who you surround yourself with, including radicals.

I've met a lot of aging Boomer Leftists who are not even homeowners, much less business owners, and barely manage to survive but understand that's the life they chose for themselves to keep tonsome revolutionary values. Shitting on a whole generation which includes its working class radicals is really misguided, as you said.