Well, of course very school is different, but it has been my observation that the people working financial aid dept for colleges are more concentrating on getting people financed (either through grants/loans), than the actual terms of that financing.
I don't blame them, I know how hard they work, and the are overworked and underappreciated, but their goal is really to get everyone matriculated to be financed (because, generally, they won't be able to attend if they aren't financed). If you want to think about it, it's like Tetris, they have lots of weird blocks of funding (grants, loans, fellowships, etc) that become available at different time to fit to the students empty coffers which appear as they matriculate and sometimes they just need to fill up a row of students because time is of the essence and they generally don't look back to see if it was optimal or not once a row of students is retired and shifted away. When it is done and the whole class is financed, they declare success and move on to their next task (raising funding for next quarter), but unfortunately it is the students that experience the indigestion that can be the result of their efforts.
The sad part of this is that most students approach educational funding the same way. If they get financed, they win, and generally don't think about the terms. People may lament the apparent unfairness of this lottery based funding system for higher education, but it is the current reality. IMO, part the issue is the fact that students often will opt for a specific educational path regardless of the cost to them specifically blindly believing that a head-in-the-sand approach to educational financing will yield them their desired result. We have sex-ed in secondary school, why we don't have financial-ed is beyond me.
Your lament seems to be reminiscent to a group of friends sitting around with some beers some complaining how some people got to have unprotected sex in high school and it didn't result in a pregnancy or some dreaded STD, yet others experienced life changing results with their singular lapse in judgement. Perhaps those that dodged the bullet, just got incredibly lucky with their inordinate risk.
Quantum mechanics tells us that end results in the universe are often only statistical, not deterministic. Since we can't live in a basement, we often need to take risks which potentially have statistical results from time to time, but we know that statistically better (but not guaranteed) outcomes result from calculated risks, not hopeful risks. We can bemoan dependence on luck, but remember, funding for anything (including higher education) is a scare resource and sometime the fairest way to distribute such a resource is by drawing straws. Sometimes you have to ask yourself if a 1550 SAT really statistically better than 1600 based on 1 sampling point taken at one point in time and if it would actually be fair to distribute resources based on a potential statistical anomaly...