I totally agree. I have no clue what his academic ambitions are, if they are lofty I'd definetly recommend a smaller school. If a certain academic program at a d1 school interests him and he wants to walk on, great. As far as transferring d2 to d1, sure he could, but I dont know why you'd want to, unless you are in a bad situation. Truth is unless you are at an elite school competing for a d1 national championship, the experience is pretty much the same.
I would always put academics first and graduate with as little debt as possible, thats my opinion. This coming from someone who is paid to win college tennis matches.