I agree that there is a sense of entitlement, however, much of it has nothing to do with paying for college. And these days, when the cost to get a degree for jobs that require one (counseling, teaching, medical of any type, CPA, etc.) are insane. The same cost of our degrees graduating 20 years ago is up 400%, salaries are definitely not up 400%. Even with what is considered very generous savings in DD 529 plan, the cost of in state tuition at any of the area colleges would wipe it out AND still leave her with a 25k dollar loan to pay off.
I do believe in the putting skin in the game. I proposed to both my DW and her ex that we have our DD pull subsidized loans while in school to cover what 529 cannot. Once she graduates, combined we can afford to pay off the loans for her. It would put her skin in the game to graduate, however, unlike a lot of college grads (including one I am mentoring) she won't have to figure out how to pay 1k a month student loan, plus rent, insurance and other living expenses just to have a college degree.