It is so helpful to have this forum to ask these questions! And get so many detailed answers. Thank you, all. 
-Vassar is on his list!
-Reed was for a while, but I think he thought he wouldn’t fit in. Talked to a friend who goes there (who loves it, but I guess he is quite different than my kid).
-Wesleyan makes sense to me. I’ll have him look at it. We toured there for our older child.
-Middlebury: is it in the prep-schoolish category?
-Brandeis: will check it out!
-Haverford: this one needs to go on his list.
I’m remembering now why he rejected a few places that are coming up. He is partial to being in a city bc we live in one. Plus, I personally would like being able to get there and back easily (I went to a college at least an hour’s drive from the nearest airport and it was such a pain). This is not a deal breaker, but it is a small consideration.