I used Unix in high school 'cause all the computer nuts would go down to the local college and use their systems to hack away at stuff. "Hack" in the traditional sense. We had Apples at school and would mess with BASIC of course, but that was just annoying really.
The first version of Windoze I was forced to use extensively was 95, and I still remember the first thought I had when I sat down in front of it. "Well this is a pile of crap." And then I went about my search for all the command line tools I'd used for a few brief months with 3.1 before the so-called upgrade. (Got the job where I was forced to use this about 3 months before 95 came out.) On 3.1, the only time I even used the windowing system was when net browsing or some such thing. Everything else I did from DOS because it was faster, easier, and it didn't crash on me half the time. Been through every incarnation since, and I've hated all of them. I'd prefer DOS if that were the only other option. Back in the day when FidoNet forums were the way to communicate in discussions if you didn't have easy Usenet access, there was a DOS based FidoNet reader called Bluewave that was just cool. No "Windows" equivalent ever came close to measuring up, and then Windows 2000 broke it completely ... not that there's much demand for FidoNet clients anymore.
I'm fairly accustomed to XP and use it at work, but I installed
Cygwin on it the moment I was able to corner an IT admin and brow beat him until he got so sick of me he just gave me admin permissions so I'd leave him alone. I don't *like* Windows and never have. I'm called prejudiced, but there's no "pre" to it.
When I converted to Linux at home, I finally felt comfortable again. I still use Windows for games and other odd things, but I find myself not even wanting to play the games because I don't want to bother booting Windows. Since my troubles with NVidia drivers began on my Windows partition, it's gotten worse, and I'm not sure I'll ever get the motivation to fix it on this machine. Some basic part of me that wants to "solve the problem" no matter what the evironment is being pulled by the issue, but even that guy has thought of half a dozen other projects that would be more interesting because they don't require us to deal with MS.