A "learning specialist" of some sort evaluated me for ADHD in middle school, but I was prescribed medication by a Psychiatrist a little while later.
The AMI I got asked me to get a second evaluation for my ADHD. I looked for a military doctor, but could not find anyone with the relevant specialty (I can't remember if it was psychology or psychiatry.)
Instead, I found a new doctor in my community that I hadn't seen before and got a new evaluation. I also got a letter from the doctor who PRESCRIBED me the meds (not the one who actually gave me the original diagnosis.) This letter basically doubts on the original diagnosis, but most importantly said that I would probably be able to do just fine in a stressful context.
For both letters, I/my parents drafted the language that we wanted as a starting point for the evaluators. They changed stuff, but I think this helped me get letters that framed my condition in a way that assured the waiver committee that I would be able to handle the academy, and later on the fleet.