yeah, dont fret the little stuff! What you cant ship you can buy at walmart. Give your kiddo a big wal-mart gift card and he will be happy
Buy your tickets long enough in advance and save his FF miles for emergency travel. I am in UA college plus and gotten a bunch of FF miles after I signed up for it (wondered forever where those miles came from as they credited them as bonus miles for flights I took months before I signed up). Get a good TA, one who has access to student fares. They often are not a lot cheaper, but more flexible than normal tickets.
Get him a rental car for the first weekend in case he is moving there by plane. Makes trips to walmart easier

And make him not visit you too often in the beginning - it really hinders you in getting good contacts in the beginning. A bit homesickness is good for forming the character