You might want to look at a copay plan from Kaiser Permanente.
I have been with them for years and when my GD and such came up, they are covering my therapy, endocrinologist and my meds (premarin/spiro).
Now I am on one of the more expensive copay plans (300/month w. 25/copay for doc visits and 10/prescriptions) but you can get less expensive plans more in your price range with a slightly larger copay that WILL cover everything trans related except for surgery.
I have to say, the doctors are all top notch that I have been seeing and the service has been second to none. I was pretty blown away.
I don't know where you live specifically but I go to the Kaiser on Sunset Blvd by the Scientology center (shudder) and my endo is the one that just so happened to start the trans clinic at the USC med center, my therapist has been working with people like us for nearly 20 years and so forth.
If you want their names or any other info, just pm me.