I'm not sure quite where to put this and it might help someone. Even one person ...
Transition Services (medical, including FFS, GRS and in some cases Electrolysis and a whole list of other procedures) is now covered by insurance in many states in the US. In Illinois, for example, I believe plans through the govt will cover most (all?) procedures for transitioning (at 60% or 80% after deductible is met with most plans having an out-of-pocket max.) In some cases there are hoops to jump through (eg therapy and 12 months RLE) but it may be worth it.
My company is on this list and is very proud of that fact. Any company on that list wants to stay on that list so they will do what they can to make Transgender people welcome.
Depending upon your situation consider trying to get into one of these companies at any level (eg Mail room, clerk, receptionist.) The insurance for the newly hired clerk is the same as the CEO. Some of the companies on that list include - Hilton, Home Depot, Johnson & Johnson, HP, Marriott, Morgan Stanley. The list is PAGES long. Go to their respective websites and find their job listings. Apply. Apply to many, you never know, one might stick. Maybe you need to work part-time at one. Be the model employee for 6-10 months then apply for a full-time position. Once in-house you will have knowledge of how to best do that.
Transitioning is expensive, that is probably not a surprise to anyone, but there may be ways to make it "affordable". For example: If I could get FFS, GRS, Electrolysis and BA in one calendar year, I would pay no more than $6000 out-of-pocket. (After about $100/month in premiums.)
Mod edit- Links advertise certain sites are against TOS 1
Where I work GCS, BA, voice, hair, Adam's apple, electrolysis, gender therapy and hormones are covered. FFS is not. Where I work it is 90% female with most of management at all levels are female and it was explained the FFS would not fly due to the why them and not me. The coverage for procedures and therapy is 70%. We have a 100% score from the HRC.