I'm just at the beginning, I am first starting hormones in the next month or so, though I do plan on going all the way as you put it. Definitely wanna get rid of the thing downstairs :-P. I am someone who identified as a gay male before realizing/coming to terms with being trans and realizing that I'm really a straight woman mentally. The dreaming as a woman thing definitely happened to me all the time, especially when I was a little younger and my attraction to men was really coming on strong. Most of my sexual dreams in that period involved me as a woman with a man.
Yeah I'd recommend talking to a specialist. Also in terms of cost, it depends on where you live. Many large cities have LGBT centers which can aid in transitioning at a relatively low cost.
And the fear of always looking like a man in a dress is of course a bit terrifying. I'm a bit terrified of it myself. But take a look at the before and after thread, or look up transition videos on YouTube. It's amazing what hormones can do. Looking at those definitely helped assuage that fear a bit for myself.