If Grandpa set up the education fund, and the trust lawyer is happy to sign the checks, then I say just stay our of this unless her seemingly frivolous ways mean that there is less money available for younger siblings and cousins. Yes it bothers you how the money is being spent, but if grandpa had all of his wits would he care? Maybe not. He might be perfectly fine with this.
When she was cut off from the health plan, why couldn’t she get health insurance through the college? There are scads of adult jobs that don’t offer health insurance. Or did you mean that she should get a job so as to be able to pay for the school health insurance?
If she missed a cut-off for transferring credits, who didn’t notice on time - just her, or were multiple people. asleep at various wheels? I have a niece who lost financial aid one year - she thought her mom was doing the paperwork & her mom thought the niece was doing it.
Has she been evaluated for anxiety? I would encourage that. And yes if she does have anxiety or an ADHD type exacutive function issue, that could go a long way to explaining the incompletes, un-transferred classes, and need for lower number of courses each semester. Given all the extra courses she’s taking for fitness, is there any chance that those could add up to a minor in something ot other?