A great question, here are my answers:
1. My doc is an endo (and female). She claims to have worked with lots of guys on low T issues, but I get the feeling that it's probably nowhere near the amount of patients that perhaps an aging clinic urologist works with. I think a lot of her work is with diabetes and other endocrine issues. She never mentioned Clomid as an option, she was recommending topical cream for T therapy, and as a secondary option, the T shots. I asked about the Clomid option, and only then did she say "yes I have some patients that do that" and she agreed to go that route with me.
2. I never asked for AI, but I did tell her I thought I was a "strong aromataser" (if that's the word), and that I felt my estradiol was high. She told me in her opinion, it wasn't a big deal or that high.
3. The original plan was a "reset", which is that we try to clomid me up, and see if it "resets" my axis. If that doesn't work, I am sure she would then recommend standard T therapy with cream or shots. But at that point, I would consider trying the clomid+AI route, whether its through her, or someone else.
4. I am leery of side effects, and AI seems to have more issues than just clomid alone. Prefer path of least dosage if it can work, but if not, would consider adding the AI. T shots for life sounds terrible, but worth it as a last resort.