At my age and in a fairly high visibility job, there is simply no way I could go stealth, too many people know me from before. However, for my day to day to life, since I live in quite a large city, I have no difficulty going about my business as a woman like any other.
With people who are introduced to me by friends, I assume they already know but I don't bring up the subject if no one else does and so far that is working fine.
What I have found most awkward was going to places like hairdressers and restaurants where I was already known as a man and then presenting as a woman but even there, it has so far gone very well and people who were calling me Monsieur not so long ago are now calling me Madame.
The best example of this was probably the hairdresser I have been going to for the last 18 months. I started to let my hair grow in Jan 2012 and had hair transplants in Dec 2012.
During all of this period and up until very recently, when I went to the hairdresser, just to get my hair colored, I was androgynous female. This lead to me being Madamed more than once by people who didn't know me but for those who did know me I was still Monsieur.
So, last September I simply explained what I was doing to the young woman who has been looking after me for the last few months to which she responded "oh, so that explains things.." with a nice smile.
This morning I went back there for the first time since then, this time in an unambigously female presentation including wearing a dress, and was greeted warmly by all the staff as "Madame".
As long as things are like that, stealth or not stealth, I am perfectly happy with the situation.
Hugs
Donna