Sorry kinda catching up. If you have been running a caloric deficit since July and have stopped losing weight it’s time to actually eat more for a few weeks. It’s called a Maintnence phase. In theory you shouldn’t run at a caloric deficit for more than 12 weeks. For several reasons, but one of them being your body’s adaptations to a caloric deficit.
I would say find your Maintnence calories, eat that for 8 weeks or so. While lifting weights. Allow your body to get out of starvation survival mode. Then do another cut.
As far as trt your insurance should cover it, as long as it’s not some sort of subscription trt service that’s out there. Your doctor saying you need it should cause your insurance to cover most of it.