The problem with GPG integration IMHO is not technical, it's practical: Most people (as it happens with tor) do not understand how it works and more specifically why it should work that way to avoid snooping and MiTM attacks. Until we solve that part, Pretty Good Privacy, won't work for most people.
As Einstein said: "Things should be made as simple as possible, but not simpler". By making PGP simpler, you're effectively killing it by adding more and more attack vectors.
As Einstein said: "Things should be made as simple as possible, but not simpler". By making PGP simpler, you're effectively killing it by adding more and more attack vectors.