Good question hon.
I think it will depend very much on the person, as you say, but as society becomes more and more exposed to us, and get more used to and accepting of us, it will gradually become easier for us to be open about our pasts. That won't happen immediately though. Medical science is wah ahead of social acceptance, and as such you will probably see a huge increase in stealthy ex-trans people, and in trans people overall. Then gradually, as those who are out and open make us an everyday thing, more and more people will feel comfortable with not being stealth. That's my fervent hope, anyway.