Yes, he has an IEP that allows him more time in school - College Board has not yet accepted the request for extended time. Hopefully the third time is the charm because it is so helpful to him. Makes a huge difference in his particular outcomes.
RE: Umass requirements - he does meet them.
Loans: agree they are bad, but I disagree with you on the threshold - for me it would be greater than $20k per year, but that’s me.
Lastly, you’re not driving a wedge at all - you’re being insanely helpful to a person that is just getting into the process - so all of your comments are much appreciated.