I went Linux years ago personally because I got too pissed off at Windows. My only Windows box was Windows 2000 for years and years - so long that friends and relatives stopped asking for help because I just didn't know the OS they were using. Meanwhile, my Linux server runs without maintenence. Still does, in fact, baring hardware dying.
My (ex)wife was the difficult one. She liked her lappy (which came with XP), but would not try Linux. Against my recommendations, she got another relative to put Vista on it; unsurprisingly it was badly supported. But she wouldn't downgrade. She also would not understand why my support of it was limited to getting it working with my/our network. It really totally mystified her why I thought Windows was not the Thing To Have. And why she couldn't sway me.