One big usability issue these days is that PGP identities come in the form of a file. Lots of people don't have the concept of that anymore.

Dunno that things have gotten much better over the years. End to end encryption is still fairly unusable to most. I think that rather than spending so much time on the cryptography we should instead work on a E2EE usability standard. Having everyone doing their own thing with respect to usability is not working out.