My personal experience made me think the important factor was clear expectations.
I was in a bit of a pickle just after graduating college for reasons of rather muddy family dynamics. My mom and I had shared a checking account. I deposited all of my part time earnings in it and just took out what I needed. It made sense. Anyway. I plan to get an apartment with friends. I'm told that this isn't okay, that my mom has a better plan, and I feel like I can't take money out of the joint account against her wishes. And I don't want to wait while earning because these friends who I trust as roommates are ready to sign a lease in the city now.
So my dad steps in and asks how much I need. He says he'll give me security deposit and first three months of rent. Everything works out fine, I take the first job I can get and carefully budget. I'm independent from then on.
Then there's my friend. The one who got the apartment with me. She's had a separate account for some time. I think the deal was her parents paid for her college but she earned money for her living expenses. She's good with money and ends up with quite a surplus at the end. She's keen on a certain position and she interviews for it at businesses all over town. She can't land anything and after some months her savings are running low. She has a trust fund. She's of age. She assumes she can access that money to tide her over. When she talks to her parents about the specifics of accessing it, there's some hemming and hawing. I think they don't want to "break the seal" and have her use the trust fund for living expenses, would rather it goes towards something like a house purchase. They end up offering her some money as a gift instead. This goes on for a year! The poor girl doesn't know how much she can spend because she never knows to what extent they'll "support" her, whether it will go on for another month and how much. It's hard to budget for complete uncertainty. She doesn't eat right because she's scrimping so much on food. She feels terrible because she can't answer my questions about whether we're going to renew the lease. Yet at the same time, she has nothing to worry about because she has plenty of money and her family has plenty of money. It never feels like it's at the point where she ought to cut bait and just take any job she can get.
My verbosity is an attempt to communicate the kind of fog surrounding the whole discussion, hopefully the reader can think of a similar family situation where things are said and yet not said.
To my mind, the economic assistance from my dad worked because it was a fixed amount agreed upon ahead of time. (Even though it turned out to be more money than I needed.) I was able to plan and map out options based on various scenarios. It was when money issues were vague that they could easily become tools of control.
I feel like this is all somewhat related to student loan debt. Many of the people I know with massive student loan debt didn't take on college costs by themselves. They had help from their parents. And it went with control of what they would be doing with their lives. I think a lot of people would reject the pressure to go to college if they could straight up say, 'no, I'm not taking on 6-figure debt I don't understand.' But when your family is making huge sacrifices to contribute to it, for some reason, it becomes messier. Think about how many people you know who didn't really think about the cost difference between colleges. I think if parents said something along the lines of, 'we've got a hundred thou to contribute and after that you're on your own,' many more people would have taken cost into account in their choice. But no families I knew had a nuts-and-bolts discussion like that.
Granted, part of the issue may be that most high school students wouldn't feel comfortable taking on low five-figure debt either, even if it was a great deal, because they have a hard time thinking about that much money. So some pressure along the don't-worry-about-it lines makes sense, but I think it's an important factor in the whole vague aspirational nature of college discussions.