First realize that USMA, can't remember about the others, will not count your scores till you do the writing test. So don't let that go too long. Summer Seminar may be the exception?
Just taking the test over and over doesn't help all that much. In our families experiences, If you are not one of those Awesomely brilliant folks of which we have so many applying to the academies, you have to use the tricks, and tips. Before you get burned out by multiple tests.
Get Prep info, and Practice books and try to get classes either through school or Private depending on your budget. ( I was told by my son's Calculus teacher that, Getting into higher level maths doesn't help much, as most of the questions do not go much past algebra). There is a lot of free or Cheap stuff out there.
Little things can make a big difference. For example...I will try to explain this right.....My Daughter was telling me about it.
When you are solving for a math problem and you have 3 answers available Solve for the Middle answer first. If it is right you have your answer if it is low you know it is NOT the lower answer, so you know it is the higher answer by default.
As opposed to starting with the lowest number and if it is wrong you still have 2 higher answers that might be right so more time spent solving on that problem.
Sleeping through parts of the exam helps when super scoring, also although I know some of you would frown on this, in some way you feel it is cheating? If the Academies are only interested in a couple area's why tire yourself out with the ones they are not interested in. I would call it good tactics, The redcoats thought the American Patriots were "Cheating" shooting at them from behind cover.
Caveat: DS that did not get accepted messed up a roll on a good composite score when he didn't finish in one subject, came back to bite him on Plan B. Of course many civilian schools are moving to Super score now.