I had PCOS and endometriosis since (my first) puberty. I didn't have the insulin issue, but did have pain, adhesions throughout my abdomen, and large cysts. I struggled with that for 15 years prior to ever starting T. I had multiple work ups (ultrasounds, CTs, 2 laparoscopies to remove adhesions and cysts that didn't resolve on their own). Once I started T, I had hoped it would take care of a lot of those issues but unfortunately, I still had pain daily. My doctor referred me to Ob and I met with a really great doctor who said that since I am on hormone replacement already and had had so many interventions over the years already that she thought hysterectomy/oophorectomy would be a good solution (provided I had no plans to go off of T in the future). She submitted it to insurance as being medically necessary because of my history and my continued pain despite a variety of treatments. I didn't have any issues with my insurance covering the surgery but I did have that solid paper trail supporting that it was a long standing issue for me (which it sounds like you do as well). I would say it is definitely worth asking about and looking in to.