I don't mean to be the bearer of bad news, but I'm not certain the wait list really works the way you are envisioning. For the past several years, the class has been over-subscribed. In other words, they exceeded their target class size. When one person declines, USNA doesn't necessarily turn to the wait list.
Over the past several years, the number of applicants taken off the wait list seems to be less than 10 or so. Yes, it happens, but its rare and I think in almost every circumstance the applicant was in a unique circumstance. The many stories of 'someone in my NASS detail got their appointment two days before I Day' seem to be almost apocryphal. Again, yes, it happens (maybe every year), but you shouldn't expect it.
My DS met with Dean of Admissions after being wait listed and before I Day last year. The Dean said all the wait listers had met the admission criteria and the Naval Academy wanted to offer them an appointment, but didn't have a enough seats. I think of it as a game of musical chairs (nominations). When the music stopped (the slating was complete), those on the wait list were left standing without an appointment.
If you look at the list of successful re-applicants, you'll find many wait listers. Being wait listed is code for 'we encourage you to try again.' I know; that's bad news, but also good news if you are determined to attend the Naval Academy.