I think what Emily says is pretty true. I live in a pretty liberal area and didn't get read as male very consistently til I was on T for maybe 8-9 months (I'm older which I think made it harder). But I think that guys have an easier time. If we are not passing, society doesn't really care. They just think you are an extreme butch lesbian or something. From strangers got maybe one negative reaction, while I was in a car. People mostly surprise me. I have gotten mostly positive reactions. I am quite out about being trans, and mostly people forget about it. I have kept the same plumber, go to most of the same stores, etc. The hardest thing was the long period til I passed but it wasn't that I got hatred. It might be different if I lived in some conservative place.
OTOH, I did wait til I was very sure it was what I wanted to do, I mean get on T. I didn't rush into it. I gave myself the time to process that I was going thru a big change.
Emily is right. I was on T for 3-4 months at work. Okay I started at a very low dose but I radically changed my presentation. The only person that even noticed at all was my best friend at work. Nobody noticed. At the end of the time there, I came out to about a dozen people. No one even suspected. It was kind of hilarious. I went from wearing girl's t-shirts (the skinny ones which show your body and girl's chinos, to men's button downs and men's pants. People just don't notice as much as you might think. They are sort of blind and I think they are more involved in their own world than you think. They don't care as much about others as you might imagine they do.
BTW, I was not really depressed when I started T, but T really helped my self-confidence. I never liked the person that I saw in the mirror. I began to really like how I looked. So it was a little boost, I'd say.
--Jay