From the examples you give, it does not seem like these types of questions would be on-topic, but I think there is a chance that they could be on-topic if worded right.
For your examples:
What are the benefits of seeing a trans-specific primary care doctor?
Seems like this one would be opinionated and probably a little too broad.
Should I ask questions about possible drug interactions to my doctor or pharmacist?
This one would also probably be closed as opinionated. It might also be too personal.
I have seen a question that I do think is on-topic that has to deal with the healthcare system though.
Should I go to the occupational therapist or the physical therapist if I have a tendinopathy in the USA?
I think question like this would be on-topic. Other similar questions could also be on-topic, such as
Which doctor should I go to if I have {x}?
Some of these questions would be opinionated, but if they are worded correctly, I think they would be on-topic.