I have to replace perfectly good hardware more often under windows than linux, with osx being the worst offender (though to be fair, hackintosh isn't what they had in mind).

With windows's new mandatory driver signing, some of my hardware will never work with newer windows. I have to either dig up a copy of 7 or XP, or throw it out. Even on 7 it's a pain. The same hardware works fine under linux.

Also, your "manually editing obscure config files" is my registry hell. I'm pretty sure every operating system sucks (I'd say OSX's equivalent is defaults.write)