Somewhat late in finding this, because Windows XT and Mac OSX might have added new factors which ought to be considered, but I still really enjoyed reading Neal Stephenson: In the beginning... was the command line. He writes easily and eloquently about the Mac/PC cultures, and he has some points I like. Some of them I have used for years in order to strike back at the mac-users (who occasionally sound more like a congregation than users of a product), and some are entirely new to me and have made me look with more enlightened eyes on all operating systems.
When I came to the end of the (very readable) book I got a problem with his opening metaphor though, where people pass by the free tanks lined up along the street in order to get the ugly station-wagon which is Windows. When you have to learn a LOT of specialised information in order to use an operating system, it isn't really free, is it? Time is an investment too, and Neal Stephenson forgets that in his delight - or perhaps this is a new love-affair, this time with Linux.
And if you follow that link to amazon: check out his fiction as well! I really like this writer.