Not griping...just trying to figure out how to advise him.
If Georgetown is truly his first choice then he should list it as #1, as for the next schools on his list, it depends.
Every year there are applicants that list schools that they really have no desire to attend only to be given a scholarship to those exact schools. These applicants then start the stressful process of trying to transfer the scholarship, not always successful.
My advice has always been to list only the schools you would be happy attending, don't try and game the system and put a lesser known school on the list you think will get you a scholarship but have no intention of attending.
If your son has schools selected that he feels he can gain acceptance and would attend those schools if offered a scholarship then list them after Georgetown. In the past they have sometimes given offers to more then one school.
One other thing to keep in mind, applicants should only select schools that they can afford without the scholarship. 4 year scholarship winners have the first year to decide if this is right for them, after that they are on contract and will owe the rack rate tuition back to the Army if they leave the program or are disenrolled, it happens more then you think. If you can't afford the school without the scholarship then there are hard choices to make if they leave the program. Again, the Army pays the full published rate for tuition, merit or need is not factored in, if by some chance the cadet is disenrolled they pay back that full published rate, it can add up fast.
Well, that's my speech on school selections. Best of luck to your son.