Well, as someone who personally waited until 25 to finally start T, and as someone who does live in the South (Florida to be exact) I feel practically obligated to come in and help answer this question.
First of all, yes, working as a woman when you are a male inside can be extremely stressful and discouraging. I personally tended to avoid any job where I had to interact with customers because my low self-esteem made me very meek and emotionally on edge (something I'm still working on, but it can be worked on.) Oddly enough, even though my first job was at a Walmart in Texas, both my direct supervisor and a good friend I met there were trans women, though they still presented as male at the time. So you'll be surprised where you might find supportive people.
For immediate support on this issue, a quick Google search reveals a few places you might be able to call up and ask for safe employment recommendations for your area. There's the Transgender Institute in Kansas City, the Glo Center in Springfield, the LGBT Community Center in St. Louis (although one reviewer does mention this has closed), and the Center Project in Columbia. If nothing else, they might be able to give you more direct advice and support as it applies to your specific state.
Was it hell waiting those eight years to finally start my transition? You bet it was. But the key is not to give up. Try not to look at what you don't have now, but instead look at what you will have in the future and let that motivate you to reach goals. Once you get a job - and unfortunately that's an unavoidable fact of life right now, having to get a job - then hopefully they'll happen to have a company-offered health insurance that covers the transition process like UnitedHealthcare. Under them, I paid $10 out of pocket for a four-month supply of T and some needles. Now, if you don't intend to move away from that job once you start transitioning, coming out may be unavoidable. Unfortunately, I can't personally advise on how best to do that, as that's something I'm still trying to do at my own work.
Anyway, I wish you luck, and I hope one of the places I listed can help you in some way.