Back in 1994, Daniel Wiese (now of Microsoft Research), Simson Garfinkel and Steven Strassman wrote a trenchantly funny book called The UNIX-Haters Handbook. Much of the material in it was culled from discussions on a mailing list of the same name (UNIX-HATERS), and the book has since been released for free with the author's permission as a PDF document.
A lot of the humor in the book doesn't come specifically from slagging UNIX, though, but from the general sense of frustration that computer users of all stripes experience when dealing with something that has been seemingly built to make their work impossible. I couldn't count the number of times Windows has done things that I found counterintuitive, or seems to have been built in some inane way. (As things have moved forward, though, many of those problems have been dealt with -- although sometimes at the expense of even bigger problems. But that's another story...)
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