One thing, my son is different (from his siblings and close friends) in that he doesn't like getting flashy electronics so likely will not open something that I gave him if I sent him away. So we are getting these these items to use at home, and get used to having them, and then he could take them when he leaves.
Here are some of the items that we may get our DS - He doesn't have a list, as he never asks for anything
* Wireless Printer (currently he shares a family printer)
* Apple Watch (not likely, because he would not wear)
* Apple TV (he has a TV in his room that has a fire stick; altho he prefers to watch his iPad)
* Winter Coat (he wears a small jacket to school even in winter)
* Winter Boots (he wears his Vans every day)
Other items (my son already owns)
* iPad
* Bose wireless noise canceling earphones
* external monitor/docking station
* fold up cushy chair
Before he leaves for school we will probably get him a computer, rolling trunk, refrigerator, and bedding)