From what I have read here this year about kids reapplying to USNA, it seems that the wisest strategy is try one's best, but be emotionally prepared for a possible second disappointment.
I would second that. Reapplying is no guarantee of an appointment, even if one does "all of the right things." There are too many great candidates and too few spots.
If they choose to reapply, it seems wise to: get the best grades possible in college, especially in math, science and engineering; get a tutor to focus on weak sections of the SAT/ACT and retake (SAT scores below 2200 seem worth retaking); do sports; be a leader in ways that matter to USNA (figure that out?)
Let me amend this a little. You need to get good grades in the right courses -- especially calc, chem, and/or physics. Retaking SATs isn't that important for college applicants; it can be for prep school applicants. USNA doesn't look at the writing section -- only the math and verbal with a somewhat greater emphasis on math. Also, sports and leadership aren't as important for college freshmen, assuming those weren't areas of weakness in h.s.
It doesn't hurt to try to get inside support in congressional offices (I saw a few kids in the DC area whose parents were successful at networking to make helpful connections.)
My personal opinion based on having served on an MOC's nominating committee in the past and having been a BGO for more than a decade is that this really NOT necessary. 99% of kids get noms solely on the merits, not b/c they or their parents "know someone." As I've stated before, my parents were actively working to unseat the MOC who gave me my nom. MOCs try hard to avoid charges of nepotism. While I don't always agree with the decisions they make, I've not seen anything to suggest those decisions are politically motivated.
I would guess that strong recommendations from NROTC unit commanders and/or from current (or even retired) navy captains or admirals (especially any who were USNA grads) would be bonuses as well.
Yes and no. Yes on NROTC if you are in the unit. As far as letters of recs from military officers/grads -- ONLY IF THEY KNOW THE CANDIDATE WELL. I cannot emphasize this enough. Finding an admiral alum who has known your DS/DD for all of an afternoon, a week, a month, etc. WILL NOT HELP. And, quite honestly, it only annoys the admissions folks who see right through it.
If you happen to have known a senior military officer for a long time such that the person can make valuable comments about you, it might help A LITTLE. That said, I'm aware of a reapplying candidate who's parent is an admiral, and many children of O-6s (Captains) who got TWEs over the past several years. And many kids with zero military ties do just fine in the admissions process -- I have 3 appointees this year and none has any military ties.
Send more recommendations than the minimum required, if you have additional ones that enhance your record.
Please don't -- unless they add something to your packet that isn't already there. Examples of "good" extra reps: most of your ECAs are church-related, so you get one from your pastor. You work every day after school, so you get one from your employer. Extra recs that merely repeat what your teachers and BGO say aren't going to help.
In the end, the grass is not always greener on the other side.
Very true. Many, many people who are crushed at receiving the TWE from USNA end up extremely happy at their Plan B -- so much so that they may turn down an appointment they received when they reapplied. And that's not a bad thing. Maybe that's what was meant to be.
There is no "magic" formula in reapplying any more than there is in applying for the first time. The sticky above provides helpful advice (from USNA Admissions) but, it's only that. It's not a guarantee.
Embrace your new Plan A. If you still have the desire to attend USNA, reapply but, as the above poster notes, be balanced in your approach. If it works out, you have two great choices (stay where you are or leave for USNA). If it doesn't, you still have the great school where you are.