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Nice contribution.
I like to learn through forums and somereally great blogs
interesting topic, jb. i actually don't consider myself much of a security expert and am never quite comfortable that i really "get it" when new vulnerabilities or threats are released. i really rely on norton to keep me protected. i often find security blogs (computer) difficult to read because of a lack of deep knowledge about a lot of the deeper layers of technology. tips and tricks, or new products - i'll search for them in the moment i'm curious about them but i'm not a big fan of podcasts or technology newsfeeds (more a political junkie on that score)... but i've been blessed with enough tenactity and patience (and search strategy experience) to find solutions to nearly every technical problem i've encountered.
for more basic security issues - don't open email attachments from people you don't know or from people you do know that don't 'feel' right - or downloading stuff from sites you're not familiar with - keeping programs and os updated - think the general message, from parents born in the 30's to my own 8 year old has worked okay. its been a long time since i've had to clean one of my 'clan's' computers of a bad threat.
maintainence education 'stickiness' is a mixed bag and n360 has actually helped quite a bit with that... before that, i could always count on dumping gigs worth of temp system and ie/browser files. older generations seem much more reluctant to mess with something that is working and a lot less curious about downloading and installing something 'new', so startup stress with these folks isn't that bad... my own kids are starting to get the idea about
now installing and operating new periphials - printers and scanners in particular - is a completely different and much less successful story. spent hours with a relative teaching her to use her hp scanner only to have to come back 6 weeks later (the next time she needed something scanned) and redo the lesson... and that is not the first one of those, which i find incredibly frustrating (important enough to ring me up and complain about things being broken but not important enough to write down any notes from what i did) in retrospect, i should have recorded the first session 
At the risk of appearing flip, the way I like to learn about security is before the event - mostly by early warning of major threats and vulnerabilities along with practical suggestions for coping with them. After working with security issues for a while, one learns how to avoid most of them by good management practice. When working with family, however, I find that despite all the tutorials, instruction, and suggestions, the most effective way to instill lasting security knowledge is after the fact - i.e, after a good disaster or two. :-<
I've also found that as much as our children may aspire to independence, they continue to be attached to us by rubber bands. :-)
-- Jim
I'm not sure that friends and/or family will ever become "totally" independent. Part of their relationship with you [generic] is that you are the expert and you can be counted on to come to their aid at any time. In a professional setting this component of the relationship isn't present. They have come to learn and you are there to facilitate that process. They are successful when they do not have to rely on you for assistance.
My current paid position has nothing to do with computer support. But, for about four years I volunteered with the same organization as a tech support person. I have gained a reputation of being able to help so I'm called on to help. I'm also blessed to have a supervisor who understands and allows these little interruptions in my daily work routine. It also lets me breathe easier since all of them carry guns :)
Back to your question - I don't want friends and family to be able to do without me completely. It would reduce the number of times I'm able to visit and the joy of being able to help. Agreed, they can be a pain but, to me, that is just a part of life that I've accepted. Just my take on the subject :)
As for the best way - listen to their questions. They will tell you what they really need to know and help you tailor your information for maximum effectiveness. Yes, you will repeat the lessons in various forms several times before all of the points are internalized but that's all part of the way they learn and you assist. In this respect the subject isn't the important part, the process is.
How do you like to learn about security and what's the best way to teach your family and friends?
This is somewhat related to an earlier post about us all being the "PC Handyman" (anyone remember that Symantec product? 
) for our families and friends.
How do you like to learn about security issues, new products, tips and tricks etc? Is it a blog, forum, a podcast, news feeds, books? Do you just play with things until they work?
Perhaps the bigger question... What's the best way to teach our kids, parents, friends and neighbours' to keep their computers secure and running smoothly?
I ask only because, even though I've successfully trained hundreds of techies in years gone by, I still spend my life supporting my family and friends and have never quite gotten them to be independent! 
JamesB
Symantec Training
Admin Edit: Subject shortened
Hi James,
Thanks for this interesting topic. I like to do it thru forum and webpage or blog that has ability to post screenshot or video clips (e.g. youtube.com, msn videos, veoh.com video etc). Most new users prefer to see than reading long guides or tutorials to learn. Videos and screenshot is more attractive to learners.
Regards,