April,
I consider myself more on the "trans" side than I do "CD" so I'm not sure if my opinion counts.
Here goes anyway:

There is another barrier that you didn't mention and it's the one that kept me from transitioning. That barrier is "physical."
My hands, Feet, and height (to name just a few) are things that no amount of surgery could correct.

Now, if it were possible for me to successfully and FULLY transition, then yes I would.
It's not, so I didn't

Your own posting has your answer, though. You told your wife that if you could, you would.
You sound rather like me - conflicted. You see the outer reality of your life but also know your inner sense of self.
The two just don't match, do they?
All you can do if decide for yourself what to do about it.

As for me, I chose the "easier" (and safer) route.
Most of the world only knows the male me. In the non-digital world, only those I love and trust even know about me as Sara. Even fewer have ever seen me fully femme.