Point blank, when I"ve been hired by employers, I generally didn't out myself. Pre name change I'd say "I go by this, not my legal name, I'm of a different nationality, that's why my legal name is that." In the past, I outted myself, and personally it went smoother to simply say I was foreign. When I did out myself, I made it clear that if they didn't want to hire me because of my trans status or let me use my preferred name, I'd find another job.
My T costs $50 for a 3 month supply, I get it online from the Apothecary shop. That includes needles.
I have a needle fetish..so I didn't need to get over the needle fear...
Bloodwork through my doc costs $40ish, but he works with people and his office visits are only $50. that varies, naturally. I have no insurance.
aND i'm on T through informed consent...so I don't know about the letter/T time.