You are in the right place to listen, read, ask questions, and learn from others experiences. A lot of the listening though that you need to do is listening to your own heart. And the one you may ask the most important questions is you. I hope you will get in to a good therapist with gender counseling experience, or at least an LGBT saavy/friendly therapist who is willing to learn, because it is hard enough to deal with what sounds like gender dysphoria when you are dealing with other challenges like clinical depression at the same time. Have you got either one of those yet?
I've been where you describe yourself, suffering severe depression, feeling you know what you need but thinking of a thousand obstacles that stand in the way. Firecat sweetie, you will be amazed what you can do and accomplish when you give yourself permission to follow your heart. You have to value the little girl inside enough to want to give her a chance. It sounds early to be worrying about full transitions or going full time etc, there is time to explore and get things right, but you can make a commitment to your self that you will follow wherever your truth may lead you.
You don't have to be ready to do what I did and jump into deep water to begin with; most girls take their time and explore gradually.
There are lots of things that you can do to explore your feelings and gain experience. For example, most decent sized cities have one or more crossdressers societies or social groups, that support one another and get together regularly to go out en femme and enjoy camaraderie and safety in numbers. If its not your town, you don't need to fear outing yourself prematurely. Many towns and cities have ciswomen or transwomen who are expert crossdresser coaches who will for a small fee give you a safe and supervised introduction to crossdressing including hair, makeup, shoes, walk, talk, and let you take home your clothing and makeup kit (or rent you storage space). For example, there is a cis woman where I live who adores transgender women and crossdressers and has her own retreat/shop/meeting space, and who has helped thousands of trans women, and crossdressing men, get in touch with their inner woman or femme, safely discretely and respectfully. There are also a number of very safe, very well respected annual conventions for crossdressers and transgender women where you can discretely try out your femme style in a safe environment for newbies. Taking a vacation from your male life might give you the boost you need, and can be done safely without having to do it all on your own.