I find that it's a really good idea to try to understand why people prefer the systems they do. Be sympathetic, get inside their heads, and you'll be better able to both defend your own choices and sympathize with theirs.
This part really should be obvious, but on Slashdot it's not: if you ever conclude that anyone likes any system because "they're stupid", go back and try again. For non-techies, a dirt-simple, friendly, easy-to-use system that does the tiny set of tasks they need is genuinely more useful than a powerful, complex system that they don't have the time or inclination to learn about. Not everyone derives pleasure and satisfaction from figuring out complex systems, and many people simply have other things to do with their time.