Another brief update... too late tonight to get into anything detailed, but I've had this kicking around for quite a while and just remembered it.
During orientation in Chicago I noticed that most of our group were well-advanced of the “all-caps email” level of technological savvy. I'd noticed this at the Archdiocese, too. There are plenty of folks now who do know what they are doing, but there aren't many non-technical resources aimed at them.
So, I decided to start with the folks most in need, those in “smart enough to get themselves in trouble” territory. (I'll be submitting an RFC on this classification system at some point in the future.) It seems like computer security is the second big learning curve for casual tech users; it requires a very different mindset than the “nothing to fear” tack we usually take when educating new computer users. The idea here was to keep to one page, clear and jargon-free, with practical advice.
So, if you have a moment, take a look at Computer Security Basics (PDF) and let me know what you think below. I'm open to any improvements you can suggest. It's share-alike, so once I've incorporated corrections and clarifications, etc., I'll put up a couple editable formats.