I get told by web forms regularly that my email is not a valid address and even people that got my email written on a piece of paper have replaced the .email with .gmail.com cause “that couldn’t be right”…
That’s the thing that holds me back from a non-standard TLD, as much as I’d love to get a vanity domain.
I’ve got a .org I’ve had for over 20 years now. My primary email address has been on that domain for almost as long. While I don’t have problems with web-based forms, telling people my email address is a chore at best since it’s not gmail, outlook, yahoo, etc…