Help: Narrowing Private Middle/School Fit (New England / NY Area)

It seems to me (I don’t really know the ISL schools) that you are only looking in a narrow band of schools – any one of which will provide an excellent education. I don’t think you can really cross any off your list, or move any to the #1 position using your list of questions without visiting. They are all excellent schools and there honestly isn’t a vast amount of difference between them. I’m really only familiar with Hotchkiss in your list of schools, so I’ve put my comments above in caps as they apply to Hotchkiss (at least in my opinion).