Sarasota a wonderful town too!
Sorry I can’t help with the Southeast part of your quest, but you mentioned being open to comments on his list in general too.
along with highly residential, generally liberal, open to quirkiness, low/no Greek or rah rah sports culture, etc., all shouts “Earlham.”
I’m very familiar with Rollins College in Winter Park and IMO there’s nothing about it that strikes me as compatible with a “quirky” kid. The atmosphere is very rich-kid, mainstream preppy.