As for GPG, https://gnupg.org/download/index.html
http://gpg4win.org/download.html for windows
http://gpgtools.org/ for mac
Go send me an encrypted email and I'll reply. I'll leave it as an exercise for you to find my public key and my email address. Or you can encrypt a message and send it in a PM. A lot of bitcointalk members do that.
As for other skill sets, I think, if you managed to do okay with SQL, you'll pick up bitcoin fast. All my resources were from this forum or anything I can find in google or the wiki.
The rest, well, I believe a lot of old timers were basically self taught. While this forum has a lot of noise, you'll find good stuff around here.
Thank you, Dabs. My evening's work (um, after the New Year's celebrations) yielded only a GPG/email working withing my new website's boundaries only.
I run windows, so I will try that http://gpg4win.org/download.html for windows.
Then:
Saturn643's comment: The simplest way to encrypt emails with GPG/PGP is to just write the email in another text editor, encrypt that text using whatever GPG software you are using, and then copy and paste the encrypted text into the email as the message.
So, I will do some homework and be back...
Try using gpg4usb from this website.
http://www.gpg4usb.org/download.html
It's portable and easy to use. All you need to do is unzip the zip file and double click the exe file in the unzipped folder. It's got a built in text editor and simple buttons on an intuitive GUI that do almost anything you need. I tried gpg4win but found this easier to use.