My DS has a friend who sounds very similar to your son, and he is very happy at St. George’s so I think you are probably on the right track. The other schools kids with similar profile we know landed at are Blair and Millbrook, and also Trinity-Pawling if he is open to single sex environment. Westminster also seems to be open to a lot wider range of kids but everyone we know there is a serious athlete. But that’s my impression of Taft too, in fact I have been told Westy is a slightly less competitive and gentler version of Taft. Definitely worth looking at if Taft is on your list.