Some aspects of my life would have been far better if I had transitioned back when Nixon was the US President. But... I have also considered the fact that, although many countries (including the US) gradually passed laws during my lifetime to help establish more equality, and much of the world is starting to understand we are all just people, I enjoyed male privilege for a half century. I didn't understand it at the time or appreciate it, but things I was sort of aware of are now much less abstract now that I'm experiencing it.
Would my career as a woman have been the same? Should be, but the statistics say otherwise. I've spent many years working for the same company with excellent diversity and equality policies, but as part of my job I often interacted with other companies in locations around the world with different rules, and doubt I would have enjoyed the same level of access. Business can be competitive and I'll never know at what point I would have received or missed opportunities if my path had been different. And so many things I never previously thought about... exploring neighborhoods good and bad at all hours while traveling. Getting quite drunk after work in cities and places I didn't know (I stopped drinking in 2003), and not regretting anything at the time except the bad hangover. Renting a car in a country where women were not allowed to drive. Landing business deals where a guy is assertive but a woman doing the same thing may be described as too pushy or worse.
I find it interesting how guys are so polite now and strangers start casual conversations, but when I actually have something to say people talk over the top of me. This started when the misgendering stopped and it's not a coincidence. There's a social dynamic I've heard women mention and I used to think yeah whatever (as I probably talked over the top of them) but I now see the differences are very real. I'm not saying those are reasons to delay transition once someone knows it's the best answer, but I can't deny the fact I enjoyed some benefits I would not have had if I'd transitioned at an early age.
An easier life for me would have been one or the other. Transitioning very early, or a body with matching brain-gender all along. But it would have been a lot less interesting. I'm okay with the way it worked out.