Our experience with USNA's admissions office was extremely professional. They contacted my son when needed but certainly did not "court" him, nor do I believe it is their job to court an applicant. The last thing the they should be doing is making a candidate feel very "wanted" when in fact the admissions people may see something in the candidate that makes them feel that maybe it is not the right institution or even the candidate may not want this as much as the parent seems to think.
Admissions officers walk a fine line when it comes to contact. As someone who has conducted admissions interviews for another institution, you need to be careful of giving the wrong impression and leading an applicant to draw an incorrect impression/conclusion.
As candidates, it is a great feeling to "be wanted" however in reality the one who courts the strongest may not be the right place. Make sure that "he who wants you" also is the place that you truly want or you are setting yourself up for disappointment.
I have had a child on a waitlist for an Ivy and they certainly did not keep us informed at every step of the process. She sent a card in stating that she wanted to remain on the waitlist and at the end of June cleared said list. She figured that we wold hear something when they had something that she needed to know. Sometimes taking a step back and letting the system work is the right solution. Needing your hand held through the entire process may not lead to the best decisions.
The military is not going to keep you informed of every item in your path, nor are they going to hold your hand for every move, promotion, or job. No time like the present to get used to handling a situation without needing to be coddled.