I know a bunch of kids who attended Westy including my nephew who graduated in the spring and I am good friends with an alum as well as a few board members. The kids that I know who attended had a good experience there. I’m not sure that I’d compare it to Taft though. It is considerably smaller and has a fairly high day student component. That may be a plus or a minus. Another nephew graduated from Taft two years ago. It’s a more competitive place. If you end up leaning a bit larger than Westy with a similar student body to Taft but with a bit easier admissions and solid educational support I’d look at Kent. I’m biased because I attended as did my son, class of '17. Kent helped him develop his interest in math and science and he’s now a senior in college studying Chemical Engineering. I know a bit about Hotchkiss too, having had a son and daughter attend there, but it’s more like Taft. If you have any questions about it, pm me. FWIW, my neighbor’s son graduated from Millbrook last spring and I couldn’t be more impressed with the support that they provided and his evolution over the years there.