And get his DD214 asap, because they seem to need it alot. Double check, get in writing how long he gets to keep Tricare and the payment plans for it.
Bears repeating a few times. I assume he's already made the SGLI decision. Pound into his head that he has benefits coming that he might not think he'll ever use but he needs to learn what they are. Specifically educational and home purchase bennies. It ain't welfare, he's earned them.
And thank him for his service for me, won't you please?