Hi Bari Jo,
I transitioned at work at 55, with 6 months of HRT under my belt, and into an environment where most of my colleagues have known me for at least 5 years, some as long as 20-30. So I do my best to look my best, but I feel like I don't have the luxury of passing, at least for now. Whenever we go out, I always assume that everyone that sees us, or serves our table, clocks me. The truth is that some of them probably don't. I can't really tell most of the time, and I'm trying not to feel condescended upon every time a server or cashier make a point to call us "ladies."
Some of the "basics," like HRT, laser/electrolysis, will make differences in your appearance, depending upon how lucky you are in the genetic lotto. I'm 6 feet tall, and about 250 lbs, so it's going to be harder for me to blend in than someone who looks exactly like me but is otherwise 5'2" and 100 lbs. That imaginary person I just mentioned, that I can't compare favorably to? She doesn't exist. So I don't sweat her anymore. Concentrate on becoming the woman you're meant to be. If she has surgery or other augmentation, that's great.
My goal is now, try to have cis-woman problems. I, for the most part, now have mostly the same kinds of problems that many cis-women have. To me, that's pretty much the end of transition, or maybe the transition to evolution. Talk to cis-women and find out how many love their bodies, their hair, their partners, their jobs...
I suppose my final word is "Who is going to decide when you're good enough?" You're never going to pass your own scrutiny. The people closest to you, the ones who know your story, you'll never pass for them. So are you trying to pass for people that you don't know? How can you really know for sure whether you pass by them or not? You are probably always going to be your own worst critic. Just be sure to be kind to yourself, as your would for another.
Erin