You have no idea how much I sympathize with this.

What's worked for me is to find queer stylists (not necessarily in a queer salon) or to ask other queers for recs -- one of my stylists was a trans woman (absolutely fantastic and I think I crushed out on her big time in large part coz here was someone who understood me instantly after years of my dealing with gawdawful idiots) and my current stylist is a jaded, totally silent gay man who completely "gets" what I want hair-wise and has little to say except for some mutual eye-roll bonding brought on by the occassional acerbic comment on the goings-on with the local queers.

To get to this point though, I went through years (no exaggeration) of dealing with stylists who'd either mess it up big time while treating my request like it's some alien / awful thing or tell me nonsense (this mostly from men) on how I'm "so pretty" and so why do I want to cut my hair short in a way that apparently makes me ugly Before moving to my current town, I finally found a (straight male) stylist (on the rec of another queer) and he was fantastic -- I'd drive 250 miles each way to get my haircut coz the folks I'd tried out in my current town were just awful. Until of course I met my current one and the one before him.

ETA: As much as it sucks, if you can, go to the queer-friendly place -- the relief is palpable I promise.