I'm working through the irony of your finding GPG easier to use once it landed in emacs. I mean... Emacs for God's sake.

In all honesty, however, part of the "difficulty" of GPG is really by design. You need to be deliberate about signing and encrypting because security should be a careful and deliberate act. If you're hoping for the program to take care of it transparently, you're probably not being safe enough. At least Emacs requires you to go through an explicit process. As you have to do with everything in Emacs.