Feedback on final application list for the pickiest applicant ever...who needs merit $

Wanted to do a final wrap-up for stressed out families who may be in a similar situation and searching. I listed the Eckerd, Wooster, Denver acceptances and merit awards above in #49. He added:

University of Puget Sound - Trustee Scholarship ($25000/yr - $100000 total)
Dickinson College - John Dickinson Scholarship ($20,000/yr - $80,000 total)
Occidental College - Honors Scholarship ($10,000/yr - $40,000 total)

As far as stats, his midyear grades were straight As, so that did give him a push above a 3.8UW (although all apps were in, and only three asked for midyear reports). He also did interview with Dickinson, Occidental, Wooster, and Eckerd.
He did not get into Brandeis. We assume that’s because we had not even visited (though it was scheduled for April!) yet, and really had done very little to express interest. Not a huge surprise.
He got into UMiami, but received no scholarship money at all from them, which surprised us…except we discovered they’d made a massive mistake in their financial aid office and it took multiple calls to get it fixed, which is likely the reason? Although, reading the accepted students thread, merit scholarships there seemed to be unpredictable this year.

He got waitlisted at American. That was shocking and really bothered him, although we had prepared him it was not likely going to be a possibility even if he got in, bc of $$. Obviously, still not sure what happened there.

And the winner is…Eckerd! We went to an Accepted Students event and it absolutely sealed the deal for him. Thrilled that he won’t be thousands of miles from home, after all of these other options!