I've heard that after a while on t (not sure how long, probably varies) that your ovaries can begin looking poly cystic (multiple "unruptured" follicles) and that that can be painful. Also, for reasons mentioned above (could increase risk of cancer but they aren't sure, psychological reasons (not wanting to get a pap which is unsafe, just general discomfort with knowing those organs are there)).
I had a hysterectomy about 5 months ago at about 15 months on T. I had always had endometriosis and poly cystic ovaries though. I had had a couple surgeries previously related to those issues and the pain didn't get better once the normal functions of those organs were stopped with T. So, for me, insurance didn't challenge it since I had a concrete paper trail of issues going back almost 15 years.
If you do have PCOS type presentation, that should show up in an ultrasound.