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I remember a text written about all the back-ass-ward analogies used in the Windows system early on and how they lead to more trouble later. There was a whole section on how the user is trained to name files and how the system names them (both difficult to explain).

It would be nice if someone pulled together the major educational works on computers and built a definitive work designed for IT people to teach them how to train less educated end users. An agreed upon use of analogies designed from the ground up to be complementary to further education. This way the user's past experience would facilitate the process.