I've met several IRL. One works at a local university and I've not interacted with him much. One is a local eccentric who likes to wear pink halter tops and Daisy Duke, cutoff jean shorts; he's severely mentally ill, and as shocking as this sounds, I'm one of the few people who's actually kind to him. One is my friend's stepfather's friend from Kentucky, whom I only know in passing, but he's been a troon since the 80s.
And then there's just the random ones you see around large cities; for example, not long before the Coof hit, I was in NYC on business. Took a train into Brooklyn and wound up sitting across from a young, visibly-distraught, goth troon. He was wearing Manson eyeliner, fishnet stockings, and what looked like his mom's black dress, whining on his Obamaphone about not having any heroin and not having a couch to crash on that night - and by whining, I mean literally a whine; was doing the "buuut moooOOoooMMm" voice and everything. Felt kinda bad for him, because the kid couldn't have been older than about twenty, and I'm sure it sucks being homeless in the middle of Brooklyn, tranny or not. But unfortunately, I made eye contact with several other riders; we stared at each other in silence for about ten seconds, then we all started grinning like idiots, then and we all burst out laughing. Couldn't help it. It was just one of those moments.
But the most trannies I've ever seen were at Bronycon in Baltimore. I mentioned this in some other threads, but the first couple of nights there were more far troons than there were actual women, and even at the height of the "family attendance" period (Saturday afternoon and Sunday morning, when moms and dads are able to bring their infant daughters down for a few hours), there more probably still more trannies in attendance than there were little kids.
And that was just counting the obvious ones, the ones who were going out of their way to dress girly and wear Pride gear; there were likely even more who made no effort at passing.