While HTTPS is taking over web traffic, encrypted email could be considered a failure, at this point. I wonder what percentage of emails are encrypted using GPG. Based on my experience it's probably less than 0.001%.
For one, GPG tools are difficult to use. Anything beyond a simple 1-click-setup-ready-to-use-including-keyserver-publication will make any wide market adoption difficult.
On the other, the GPG standard is a bit ... clunky. Ideally it should be modernized to take advantage of the email format; add generic messages about encryption in alternate mime content bodies and simply encode the encrypted messages into it's own. I imagine other, similar, improvements could be made, up and including having GPG also sign the email headers before pushing it out into the world.