The difference is that a hippie who got bored with a commune could get a job and in less than a year had disposable income to pay for goods and services.
Now take a 20-something today who gets bored playing fortnite and decides to get a job. It's the same as the hippie, except a) they have something like 50K of debt (and rising), b) from day 1 their place of business starts getting telemarketer calls for student load consolidation, c) debt collectors call their employer in an attempt to intimate and harass them, d) at worst their wages are garnished to pay the interest on their loan, e) they are depressed because of a-e. (Aside: when that employee leaves the organization the debt consolidation telemarketers very quickly cease calling, which is super creepy.)
That last point about depression is key. Imagine the existential crisis of a hippie who must challenge their idealism and come to terms with the much more limited (yet realistic) freedom that comes when working for a living. Now for the fortnite player add a sense of interminable dread from a sea of debt that cannot be unloaded even in bankruptcy. The small joy of choosing what to do with the money one has saved is gone when one cannot save any money.
I can't think of any persuasive argument that says the hippies wouldn't have been swimming in debt if college had been funded that way in the 60s.
Upshot-- I can't figure out the source of your mixed feelings. If students today are entitled, they are no more entitled than previous generations of students who didn't deal with this kind of debt crisis.
Anyway, a critique of a human institution almost always involves humans who are not acting responsibly. If every institutional critique devolves into a discussion of how irresponsible a critical mass of the actors are, what's the point of doing the institutional critique?