In many ways, it's a tough question, yet easy to answer. First of all, it is different than anything I ever imagined. Back in my cross dressing days, I was obsessed with so called "passing." Now I'm obsessed with looking the best I can and letting the cards fall where they may.
Along the way, I have crossed so many frontiers, they are hard to remember. Communication barriers arose the more I lived as a woman. Both genders communicated with me different. For the most part I was ostracized by men and treated with curiosity by women. Along the way, I just came to expect it. I learned to be more of a listener and be on the outlook for passive aggressive behavior.

"Passing" was also replaced by comfort and blending. It became simply impossible for me to put together a complete "heels and hose" outfit for every occasion. Instead, I began to dress to blend...with other women. So, again, I was dressing for women and not men.
I think too, in many parts of the country, living as a transgender woman or trans man is becoming somewhat easier. In fact, I recently gave job advice to a new trans woman friend. I asked her if there was a Kroger Grocery Store near her. At least around here, Kroger makes it a point to be very diverse.
Not to say life is a piece of cake for a trans person, but in someways there is a glimmer of hope on the sunrise. Especially with the political situation beginning to change. Even in Alabama.
Finally, if you really are thinking about going "full-time", dress to blend and go to the hardest places you perceive to go. If you can make it there, you can make it anywhere!
Good luck...on your new gender skill.
When I came out to my family, my then 15-year-old grandson had two concerns: Would I leave his grandmother, and did I still like football. No, and yes were my answers, and everything was cool. I hope this cross dresser can open his mind as much as a 15-year-old.