You actually just need a reliable way to get information from them once plus a good cheat sheet (see above comment) on GPG. So, you both use cut and paste to (a) generate keys, (b) add keys, (c) send messages and (d) receive messages. Exchanging the key file is the only step that requires slight thought and there's a dozen ways to do that.
I still don't use or fully understand the web of trust model as I haven't studied it in ages. I do use GPG every night with the right person on the other end, though. Still don't know anything else about it. Don't want to, either.
But then a friend tries to be more secure and sends something using --throw-keyids or --hidden-recipient. He tells me I should use --try-all-secrets, but adding that to enigmail doesn't work. I still don't know why.
I'm trying to do this with some friends, and we keep on running into problems like that. Everything turns out to be easy to solve, but only if you know exactly how it works.
You'd have to be an idiot to read those command names and try them. Whereas "gen-key," "import," "export," "-e," and "-d" have obvious, low-risk usage. More so if you cross-reference against the docs.
On top of that the interface is atrocious, go find someone with an image in their pubkey and try to display it from the command line.
Good luck.