Oh, Goro. If only it were ever that simple.
The New Yorker approach works in New York, where you can be reasonably sure not to have to deal with the same jerk quite so often. One can be just as brisk as one wishes and not have it come back to bite you. Hospitals and medical schools are much smaller worlds.
Also, there really is a big problem of health care workers not knowing jack about trans issues, which is a big problem when we present for care. I have been treated pretty terribly on several occasions in the offices of professionals in whom I was placing ultimate trust. And that is not an uncommon story. Some of my friends who are trans have had me accompany them to medical appointments just so that they would have some support for their boundaries with the provider.
On one occasion, I went with a transgender woman to the ED when she was having an acute asthma exacerbation. The ED nurse couldn't focus on her chief complaint of not being able to breathe properly, because she was too busy asking personal, sexual questions. I called her on it, politely, and said that I would be happy to meet with her for coffee sometime and she could ask me everything she was too timid to Google, but that she was being inappropriate to her patient. She said that it was a teaching hospital, so she was allowed to ask whatever questions she wanted, and she continued disrespecting my friend until the end of her shift. My friend was humiliated, but what do you do when you are in extremis and the person who you are looking to for help is too ignorant to realize that their "curiosity" has become abusive? One could argue that asking a patient about their sexual habits is valid when taking a history, but perhaps mid-bronchospasm is not the ideal time to ask whether the patient is able to experience orgasm and under what conditions. (I wish I were exaggerating.)
Scenes like that are a big reason why I am going into medicine. There is a terrible disparity in medical care access for transpeople, and a big part of it is due to providers having earned the distrust of patients. Not because they are terrible people, but because they are genuinely deeply curious about an uncommonly encountered phenomenon. I have a pretty thick skin. If I can be the one to teach someone about trans issues before they run into a patient and humiliate them, then it is worth a little discomfort on my part.
EDIT: Took out my gentle criticism of your use of transgender as a noun rather than an adjective. While to my ear it has a certain nails-to-chalkboard sound, upon reflection, it is no more wrong than calling referring to someone who is German as "a German." Still, to me, the construction sounds more like talking about someone from England as "an English." Not definitely wrong, just somehow not quite right.