As much as I like the idea of running a TLD, if anyone gives me a TLD, I'm gonna put an MX record on it and be jonah@org. That's a promise.
EDIT: To be fair, I would probably be overwhelmed with the usual sense of responsibility and not do this. But, the temptation
So one night, a new ham is operating his friend's fancier station, which has the HF equipment to talk clear around the world. And they make contact with another ham identifying himself as JY1. No suffix. Well that's weird, so they look it up, the JY prefix is Jordan, okay. So the guy on the mic just asks, "why doesn't your callsign have any letters after the digit?" and the reply comes back with a chuckle, "Oh, because I am the King."
That was the late King Hussein. about whom much has been written. I don't know if his call ever caused trouble with software validators, but I'd certainly believe it.
Took a while to get ARRL Logbook of the World credit for that one.