Many of us are to the point where we are more or less fearless going out en femme and many of us have gotten to the point where interaction with others is not a problem either. Other folks are either unaware of who we really are or are aware and don't have a problem with it.
That having been said, what do you really want after you go out and successfully pass and interact as a woman? Do you want to go further and actually become a woman with or without transitioning, or are you content simply becoming a part time gal? If all responsibilities and encumbrances were removed from your life, would you proceed to transition without hesitation or do you still enjoy being a man too much?
Even though I enjoy dressing, I now make it an occasional thing, even though I really have nothing to hold me back from doing it full time. For the first time in my life I'm enjoying being a man who can express his feminine feelings any time he chooses. What do you really want from this?