My best friend and her husband let their 4-year-old pick out his clothes, so sometimes he looks crazy. But ... he's 4 and who cares? As long as it's weather-appropriate and clean (he has two t-shirts that are his favorites and sometimes they have to be like "but that has a stain on it from last night's dinner, so put it back in the hamper"), they're good with it. Scott could take the same approach with his kids.
I went to an Ivy and a classmate of mine, who had gone to one of the best boarding schools in the country, fucked up his grades the first year. His father was like, you have ONE semester to turn this shit around or I am dragging your ass home, and you won't be sitting around my house feeling sorry for yourself either. If you want to fuck up, you will not do so on my tab. (He did turn it around, though he had to take a couple of summer classes after we graduated.) It wasn't about money - he came from a really wealthy family - it was about ... not fucking up. Like, yes, you're a legal adult and you should have some fun, but your job is to go to school and do well, and you are not doing that. At all. And that won't fly.
I have a family friend who got into an Ivy, fucked up the first year, and her parents pulled her out and she finished her degree at a state school while living at home.
It surprised me to hear that about Simone and Cecil's son, since he seemed to be pretty academically inclined. But maybe the freedom was too much for him.