Michelle,
You bring up an excellent conjecture: "...perhaps I am better off with no secrets and fewer, but true friends."
So, you or we can have the situation where we generally pass and are accepted until someone outs us, then most of these same people we socially interact with are misgendering us and the relationships go south.
Or we can preempt all of this outing by just being upfront and tell everyone we are trans-women. Exactly when to out yourself seems problematic, it could be awkward. That does not seem the way to go.
It seems to me that if one passes well and is accepted as a woman, just blend in. Tell people at a trans related seminar or workshop that you are trans, or by them attending, they may already know that. Tell your physician, someone you have an intimate friendship with, tell family, people that knew you from your deadname years that you want for them to know, but for everyone else, do not mention it! Maybe tell them if they ask you about it. If they learn of our trans-woman status in any way and are not accepting, so be it!
So perhaps you, or most of us, would be better off with fewer, but true friends.
After all, how many of us have lots and lots of real, true friends any way?
Good thoughts Michelle. I really enjoy your posts.
Chrissy