We went through this with my son and his application to West Point last year.
Bottom line, based on his experience, is that if they want him they will submit him for a waiver. Good luck as the application process can be a long drawn out affair (we were still submitting paperwork in May when Reception Day was just weeks away, and he had let all his other college opportunities go by the wayside). Worked out in the end though.
If he is submitted for a waiver, I'd suggest keeping on top of the DODMERB with frequent phone calls to see where his paperwork is etc.
Again, good luck!
I have heard that it is a good idea to stay on DODMERB during this process. He is applying to a number of excellent schools, but second best is a distant second to the USNA. Thanks for the advice.