Your point is a good one, FA - I definitely think transitioning when I did hindered my dating confidence. I'm pretty sure I wouldn't have been able to get used to..."it"...lol...so sexual confidence wouldn't exist for me. But there is something to be said for the fear of someone finding out your genitals aren't what is to be expected. It makes me feel bad about myself, and like no one will ever love or desire me. I don't even know if I could stomach telling someone what I've got going on (not because there's anything wrong with it, I just hate it so so much). But if I had experiences dating and being loved, perhaps I'd feel more at ease about telling them the situation, even if I wasn't comfortable sexually.
Someone brought up the point that I was good to do this when I did, because I was in my Master's program. And you know, they're right. My job was teaching - my only boss was the prof I was working with, my only coworkers were a few other students, usually one at the time. One term I was the only TA. So I didn't have a horrible boss or coworkers to deal with, which I would have anywhere else (getting misgendered at work would have really hurt). My students, although some raised ignorant questions or said off hand comments, weren't going to screw around with their TA like a customer would with a service person. I also got a lot of isolation - I taught, but everything else I did was on my own. Marking, prep, working on my own research, etc. The first year I had coursework so my classmates knew, but that kind of thing isn't going to come up in class, you know?
So in that sense I was REALLY lucky and I should count my blessings there. The job paid enough to cover my bills and more, and it gave me a relatively safe place to transition.
Really, I think I have regrets for two reasons, and those regrets might be there no matter when I did it. First of all, I wish I was cisgender. I don't care if it's cis male, cis female, I just wish I was cis so I didn't have to hurt anymore. Second, transition put me through the ringer in too many ways, and every moment I delayed it just dragged the process out. But it would have been hard regardless of the age I did it. I think there's pros and cons to both early and late transitioning.