I'm in agreement here. I've set up PGP email, and S/MIME, and it isn't really that hard to use once it's in place. Mail clients that support it offer easily-invokable "sign" and "encrypt and sign" options. But when few people you email use it, you yourself end up using it rarely, and then you get a new computer, lose your keys, and you can't even revoke them because you didn't keep a backup. So you have to do it all over again. Then it seems "difficult to use" because you have to stop and read some man pages again.
> They're complaining in essence that PGP isn't automatic and frictionless.
Exactly. That was cryptocat was, UX-wise. Automatic and frictionless. I believe if crypto can be built in that fashion, then it will really effect the world. In expert fields, GPG is used, but no average Joe uses it.
I suspect that most of the people who say PGP is too hard to use simply don't encrypt messages that often (or, when they first learned PGP, weren't routinely encrypting messages). They're complaining in essence that PGP isn't automatic and frictionless.