You can improve the written documentation with diagrams or produce a graphic novel for the reading impaired.
There's a real opportunity to build something much, much simpler on top of PGP. All you really have to do is pick some sensible defaults and automate a few steps. Look at how many nerds can't be bothered with encrypted communication, let alone normal people.
I face this daily, since I'm the go-to guy at my office for scripting/coding solutions for these folks. They just want it to work without having to learn or understand their decisions. And these are the same people that will spend hours figuring out complex lunch accounting issues or read volumes on video game strategies or rebuild engines.
Bob has to make sure that the public key he thinks is Ann's really truly is Ann's, and not Eve's.
That would be a hard problem to solve.