Trying to please both a friend and a superior?

Ummmm, what about your dream?? I would have killed to be a DM when I was in the band (1970's). On the other hand, are you from a small town? Your director seems to be a bit blinded. I come from about 20 min outside Phia. and many HS bands have more than one DM, I've seen up to 3. I wouldn't sweat it, whatever happens was meant to be.