Not an elitist myself (yeah OTS!) but just pointing out that to charge one as an elitist and then say your 'kid' won a more competitive scholarship than an academy appointee can be perceived at best, as being incredibly defensive and at worst, elitist. Many who are appointed to the academies...
I don't think your DS made a 'mistake' in securing a Pres nom early in the cycle. My DS secured Pres noms mid-July and finished his packages by early Oct. LOA from USNA in November. In looking at last year's appointment threads, it looks like more Pres noms come through later in the cycle...