It is a similar process each year. When they issue the special issuance they list the specific requirements in the letter for the next year. It's is slightly different than the AME guide, but in the end it is two letters from the same people. It seems that there is some variation on what is in the letter for each person. From what I hear the requirements in the special issuance letter will be needed each following year. I have not experienced that yet, but I will next year.
I have a second class, but I don't think that matters much. I would still have to have the same letters every year if I did 1st or 3rd class. Although for a third class I will assume I would have to send in the letters directly to the FAA yearly instead of my AME I use.
The
transgenderpilots.org is a good place. I only found it a month or so ago.
You can always call the FAA anonymously as well. I have several times.
There are companies that specialize in getting speedy medicals pushed through. It is for pay, but there are lots of professional pilots that cannot afford to wait for a special issuance to be approved. Usually not for being transgender, but it worth looking into.