I think an equally large problem is 17-18 year olds not understanding that the way they personally might weight their stats/EC/essays is not how highly selective, holistic admissions colleges weight those items. There are plenty of schools the OP could have applied to that he would have been assured of admission and also would have had a completely transparent aid package (University of Alabama, Miami of OH, Arizona, etc). Great schools, but not what the OP wanted.
Transparent admission/aid practices were not something he valued enough to make that a main component of his college applications. Fair enough, he got to choose what he most valued - it seems like prestige was very high on that list (reasonable, it is on a lot of people’s lists).
However, it seems clear that he didn’t understand his realistic chances at these schools, and if he feels it is unfair that students with ‘lesser’ scores might have be offered an admission spot - he doesn’t understand that holistic admission means the school chooses how they evaluate and value the applications upon receipt. Someone, with say, a 1490 SAT score, with an uw 3.9 won’t be looked at as having ‘lesser’ stats by Admissions, especially if the rest of the application is incredibly strong.
Having listened to a lot of admission podcasts (Rick Clark’s is really good), it seems clear that most, if not all Admission Officers at holistic admission colleges read each application to see if the college application makes the case for that student getting a spot at the college. Admission Officers want to accept students to their school, that is literally their job. They read every application to find the story that makes an acceptance likely.
Putting together an application that makes a compelling case for admission is hard. Most ‘average excellent’ students put together an application that shows they are smart, capable of doing the work and ‘a good person’. Relatively few applications make a case that the school would be missing out if they didn’t accept this particular student.
To be clear this is a pretty sophisticated idea, crafting your college application to create a compelling story of why all the components of your application come together to require a specific college to admit you. Most students (no matter how smart) aren’t skilled enough at 17-18 to do this. Which is why Admission Officers often talk about how they could choose multiple classes of high qualified, impressive students who could succeed at their school - those highly qualified kids start to blend together so what separates a yes, from a waitlist from a no can be relatively small institutional needs, versus the Admission officer thinking one kid is clearly better than another. Very few 17-18 year olds can make a great case for themselves, and those are the ones who get admissions offers from every incredible school you can imagine.