Speaking from my experience and the experience of other post transition guys I've spoken to, medical transition is about your future and improving your quality of life so that you can have a happier future going forward. It can't fix the childhood you were robbed of, the experiences you will never get to have, or the fact that you are inherently different from most men. But is that a good enough reason not to do it?
For me, it was either I didn't transition at all and eventually would've committed suicide or transition all the way in hopes that life would be better on the other side. So far, life is better. It doesn't stop me from getting depressed when I think about how unfair it is to be trans, but it did at least get rid of me wanting to die.
FWIW, I have never heard from any trans guy who has completely medically transitioned and regrets any of it, even if it isn't everything that they hoped it would be.