Very true, I found a similar issue with vanity/hack domains too. Picked up https://jo.hn a couple of years ago and the confusion it causes isn't really worth the cool-factor most of the time!

They tend to really just be suitable as a supplementary domain for short links and the like (youtu.be, goo.gl, etc.)

I have even had people confused at [last name].io even though tech industry folks consider that one really common.

I can see why many companies end up paying lots of money to transition over to .com when they get to a certain size.