I think many 'advanced users' don't believe that there are others that need more information than they would need to learn something. For example, there are plenty of people in the advanced western economies that do not know what an operating system is. This might surprise you, and many of the readers of lwn.net, however I have listened many times to very smart people talk about how they use a computer and it is clear many do not understand the relationship between the software they use and the operating system they use. They see it all as more or less 'the computer'.
Once you get outside these wealthy nations the situation changes dramatically of course. There are many people in the world that are encountering a computer for the first time via the OLPC project (amongst others). More still that will never see a computer in their lifetime.
My point is, there is a sliding scale of understanding about computers. If we wish to bring people into the sphere of free software then we have to realise that the largest potential market, and the nearest to conversion, is the average user - one that might know what 'online music' is, but doesn't know an 'audio file' from an 'mp3'. The free software sector has to talk to these people in a way they understand if we really want to see free software on every desktop.