I think it's getting easier for each new generation. Sometimes i'm jealous at the (relative) ease of transitioning for young people today compared to 20 or 30 years ago.
As a teenager i never heard of such a thing as transexual or transgender. Even when i did start dabbling in things supposedly reserved for the opposite sex, i had no idea that there was such a thing as transgender. I was simply doing those things as an exercise in asserting freedom of choice.
Eventually, with the advent of the web, i learned about it, but by that time i had been living my choices for many years. When people started to learn about transgenderism, they started to consider me transgendered. This created a problem that i have only recently resolved by deciding to actually play the role of being transgendered, although i do not consider myself that. I realize this must sound odd...
In the end i decided that if most people considered me a woman, rather than a man who was asserting equality and freedom of choice, then it would be easier for me to play along with their expectations. Doing so does not change who i am, it merely makes my life a bit smoother and more clearly defined for others.
I don't feel that i have to pass, although (to my amazement) it seems that i mostly do. It's more just an attitude that, ok, if they consider me a woman, then i guess i'll go along with it - can't do any harm