I've talked about this a few times with my therapist. There is a part of me that wants to "Come Out" say to my sister. Especially these past few years of actually feeling good about being me. After loosing so much of the shame and the guilt from a lifetime of internalized transphobia. It's the ole, "You are only as sick as your secrets" aspect I come at it from.
When I talk to my wife about it, her answer is much the same as mine, "To what end?" There is a reason I call her my reality therapist. I have often concluded there is no real purpose, much less (overwhelming) need to tell anyone right now.
With one exception. I did need to a few back. After 3 months of getting the run around from my health insurance and doctor and the insurance companies gatekeepers over covering my HRT, AGAIN, being denied under "Age or Gender", I did a lot of digging and found our policy from work has the typical "Trans Exclusion". Ironic since I work for a multi-national, with great platitudes about being "Inclusive" and wonderfull sounding policies on non-discrimination for many thing things including gender and gender identification. After hitting a total denial brick wall after 3 months I went into Social Justice Warrior mode and talked to the head of HR about the insurance situation.
The following weeks I had to work hard at suppressing the coming out euphoria that followed. It was great that the Earth did not open up to swallow me, no lightning bolt landed on my head, everything went OK with HR and is going to try to remedy things though the broker says there is no way to loose the exclusion! WTF

I'm not planning on transitioning to full-time any time soon. In fact actually glad in ways since I am able to strike a balance with all my competing needs. I don't feel I need to transition most days, it is just a want or like to fraught with many unnecessary risks to my life today.
Things are working fine. Why mess with it?