Back when I was in HS and had an ungodly amount of time on my hands, I might agree with the 'like to set everything up and maintain everything myself' comment - in fact, I used Gentoo. But as time went on, my amount of free time fell and my time in general became much more valuable and I realized the importance of having a system that just works. That's why I initially switched to Ubuntu, which took a big amount of overhead off, and finally switched back to Windows once I realized that it was secure and fast enough for everything I need and that stuff really just does work - I can plug in a second monitor while my computer's running and it's up and going in 2 seconds; I can put a Vista DVD in a computer and have a fully working machine with all drivers, network access, and the works within half an hour.
In the end, that's why I fell away from Linux - I respect it and still like it as a development platform, but once I realized my time was actually worth something I fell away. Heck, just assume that my time is worth only my college-job salary of $12/hr. If you assume that I spend as few as 20 hours less time configuring and tweaking my Windows install (which if anything is a dramatic underestimate compared to my Linux usage), suddenly the cost of purchasing Windows is worth it.