You sound a bit like myself.
20 years ago my issues were so small I didn't realize I had a problem and I was doing fine as a man. These days I'm scared for my life if I don't do something. If only I'd known...
It would be great if you could know how things are going to turn out in the future. Transitioning has a pretty high cost, and if you can live without it that has a certain appeal. The problem is knowing ahead time, and I've no idea how you're supposed to work that out.
There may be an expectation of how things work by some, but its not the way I'm doing things. Its my road, and I'm going to find my way down it (I'm pretty stubborn). I present male at the psych and endo, and I've had zero problems with it. I'm getting everything I need, and no more or less than if I presented female. I may be lucky with where I live and getting decent people helping me, but knowing what I do now I'd work around them if I had to.
I'm sure its easier socially though if you confirm to expectations, but I've not faced that yet, and not looking forward to it either.
Basically I think you need to be yourself, if you can work out what that is.