I’m 33 but been in the Navy for 8 years as a naval flight officer. However, 95% of the units ive contacted for boards coming up in the next year, said they are considering age waivers for those that exceed. Now since I’m a prior, that may have different implications. But the attitude I’m taking is, I’m going to make them tell me no. I always preface my initial phone call or email with that and it has been met positively so far except for one ANG squadron. To clarify, that squadron wasn’t mean or cold about it, they simply said they weren’t entertaining waivers at this time.
So my advice, reach out, be direct, and ask the question. Worst they can say is no.