Dee,
Yes, it's risky and life-changing to transition and your questions are natural. And since we're transitioning from a male body it's unlikely for most of us that we'll ever be as attractive and naturally feminine as we've dreamed.
It may help to consider two states of being:
1. Remain as you are. What a relief! Except, we know that it's far from ideal and has brought up all sorts of sadness and depression for so long. It's not going to be fulfilling or come near to achieving contentment.
2. Become your authentic self, which may be a (trans) woman. I put the "trans" in parentheses because as we transition we're striving to be the feminine person we need to be to achieve sufficient relief from gender dysphoria and the joy and contentment of finally living authentically. But no matter how "far we go" we will always be transgender. Even beautiful women like Laverne Cox are and always will be trans.
The journey between "1" and "2" is scary, uncertain, and fraught with risks. It's unfair that we have to go through this but it is what it is.
I believe in taking small steps, evaluating how it feels after any euphoria has declined. Consider how contended you feel, how your gender dysphoria feelings are mitigated, and try to determine where this step finds you:
* This is enough, I've arrived!
* I don't like this, I feel I've gone too far, and wish to undo this step.
* I like it but now that I'm here I find that I wish to go further.
Then, follow your path, perhaps back, perhaps forward. And please note that it's okay to change your mind later. But what if you've done something like surgery, which is obviously not undoable. For me I was surprised and gratified to find that when I reached that point the decision was easy. Earlier, I never would have said that.
I'm sure you've heard that after transition we still carry whatever emotional baggage we had before. Maybe a little lighter since we're finally being authentic but all the other crap comes along. I think this is where I need to emphasize that mental therapy and perhaps psychological meds are so important, before, during, and after transition.
That you asked this question says to me that you know you're not content now. I know this feeling all so well. For me, I am much much more content with my life than I've ever been. And yet when I look in the mirror and listen to my voice I know that I'm evidently trans. Now, I could get stuck in the mud of these negative feelings but I try to choose not to. I get together with friends for dinners, camping, hiking. I also just started a ballet exercise class! (It's tough.)
I think that finding contentment is what we as humans struggle to achieve throughout our lives. It's a never ending journey that we wish we didn't have to take but it's in our nature. For me a cornerstone was finally acknowledging that I'm trans and then transitioning. Where will you find contentment? I can't answer that for you except to say that it's unlikely you'll find it by staying in the status quo.