Great reply and thanks for sharing. Specifically wanted to thank you for this part:
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[Aside: something that I often told my tech support guys after they'd get of the phone with a particularly 'dumb' customer was "Remember that everyone is an expert in something. You happen to be expert at personal computer technology. The person on the other is expert at something else and they could talk circles around you in that subject. So, what you are doing is teaching them your area. Have faith, they'll get better." As a result, my crew largely did not blame the end user for their computers failings.]

A lot of my own tech upbringing ended up being around a lot of the BOFH types, and it had a negative influence on me I hadn't realized until years later. I cringe around coworkers who still carry this type of negative mentality forward these days, and gently try to guide them away from it.


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Then there were the timid users, who were afraid of their computers, and these were the ones who required the most help. Some were frightened of doing the wrong thing, as though an errant key stroke or mouse click would cause the machine to die. Others just had no computer savvy, and were we wondered what had motivated them to get online.

Largely, the timid users didn't seem specifically afraid of viruses or trojans; their fear was of technology itself. The fact that there was malware (it wasn't called that at the time) bolstered their fears, but I think that they would have been timid users anyway. The technology was hard to use, on both Apple and Windows operating systems.

Great point, and I've had a lot of experience with these types of users. The security issues of Windows in the late 90's managed to help reinforce those fears in some, after having to hand over hundreds of dollars to places like Best Buy simply from plugging the computer into the internet. My frustrations from that time were in seeing that most of the security issues Microsoft had were similar issues Unix systems had already encountered and fixed a decade or more earlier. I probably overestimate the impact at times, as I was one of the people working in customer support during that era cleaning up the mess. For some customers, the only solution they accepted was refunds of the computer, and them shrugging of tech at that time. It was an interesting era to work in a department that reported direct to the CEO of a major computer manufacturer tasked with making the customer happy after the most extreme of problems.

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Anyway, rather than Windows' lack of security, I'd say that the problem was the difficulty of use. "User Friendly" was an oft touted phrase back then and while it undoubtedly helped sell whatever was being marketed, it was almost always a lie. Everyone reading this can think of countless times that a piece of software has behaved in an unexpected way. User friendly, my eye.

Very true. When OS X came out, it attracted my attention because it was Unix. I had spent a number of years prior to 2001 learning more about other Unix variants like Solaris and BSD. What I quickly fell in love with was the true user friendly approaches in the system. This came in more from programs like iPhoto that Apple bundled. Plug in digital camera, photos show up on screen, and one button away from importing them to the computer. Management of the photos was then done by people manipulating the photos instead of the files named IMG_0001.jpg. All that file structure still existed, but was abstracted away from the user. People who still want to manage and work with the files directly still could, by using the Image Capture app to import off the camera instead of iPhoto. Power users were empowered with smart folders that could allow them to replicate some handy organization aspects of iPhoto. Later full RAW support was added at the system level, continuing to empower the pro photo taker. An OS and bundled apps that delivered a solid photo management solution to users of all skill levels in 2002-2005 left a lasting impression on me.

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those early days of 14.4kbps dial up using Trumpet Winsock

Thanks for providing fuel for possible nightmares tonight wink (My early tech career was at dial-up ISPs, initially on the support side before jumping to the admin side.)