<p>Since many have addressed the academic stuff, there is more to college than splitting hairs at two top places regarding math excellence. E.g., living environment Boston vs New Haven, is he big town small town? Boston would offer more from my perspective. In the end I don't really see how you can lose, and are very lucky indeed. Good luck whatever he chooses.</p>
<p>You will drive yourself nuts trying to stack up the pros and cons between H and Y. In this case, it really is best to go with the gut after an overnight visit. At one of the schools, he will have a stronger "these are my people" sensation, and that's where he should go.</p>