This sounds very similar to my life, I started crossdressing by the age of 4, so I have always known I was a girl.
I grew up in a small mining town, in a period of time that was full of people that hated gay people. I could never have come out, but now still living in the same town, it's a different story.
I learnt to fight growing up, no other option, seeing others always seen something different about me! do I care NO! Seeing that I am 6 foot tall and quite strong I don't really have issues with the bigots in this town, plus I have a nasty streek for getting people back for things they do to me. This comes from my military training, join the army, travel the world, meet interesting people, then kill them. The same for any military, this is how they train people. But not the way to live in my book, but I can defend myself, that's for sure! Personally I don't like fighting, but I will defend myself. These days I have no problems with the locals, they have learnt not to piss me off.
I am the same as you in many ways, as your post read very similar to my life story. Finding out as a teenager that a sex change operation was possible, made me want that more and more, but life didn't work out that way. So like you the fantasizing continued for many many years.
It is only with the help of my wife that I am able to sort myself out, and my wife is willing to live with me even if I am a girl, very very lucky I am. My wife is the only true friend that I have, or have ever had! She means the world to me!
I like you feel more comfortable around other women, than men, even though I still have a few male friends( I have a mate visiting today to clean his gold out of his mercury and to do some art, seeing we are both artists).
I grew up in a Christan family, so in no way would I have spoken to any of my family members about how I was feeling , so I buried my feelings about who I truly was, real bad mistake that was. Depression has been with me most of my life, and I only ever felt normal when I was dressed as a female.
After some issues within the workforce I suffered with depression again and boy did it dump on me! All the problems compounded my issues to the point I now have to do something about my problems, no choice!
By not being able to be me and growing up in this town and backward state has made me angry within myself, this rears it's ugly head when I don't want it to, so I now need to fix me, to make me happy and to make me who I truly am!
You sound like me, a true woman hiding in a male body!
Find a support group and see a councilor, is what I'm in the process of doing, as I see this as the only way to sort myself, maybe the option that you need to look at.
As far as money go's get a job or 2 and save as much as you can, I have other ways for myself, as I don't have a job as such as I am the stay at home mum to our 5 month old boy, but I do have a car that is worth about 70k plus, this I am happy to sell so that I can be me, even if I have had the car for 25 years I will sell it!
I need to be happy the same as yourself, so I understand exactly how you feel, you are not alone!
Do what ever it takes, don't let money stop you from being happy, be you and be true to yourself, then you will be truly happy!
It has taken me 40 angry years to start sorting myself out, the anger and frustration I wont gone, I want and need to be happy for once in my life, I don't want another 40 years of being unhappy and not being who I truly am!
So don't be like me, don't hide your problems for 40 years, deal with your issue so that you can be happy within yourself and spend more of your life living it the way you want.
So just do it i say!
Life is too short so live it!