I left Windows when XP was released. I was tired of ad-laden spyware-bundled software that I couldn't manage and update centrally (i.e. each piece of software was nagging me for updates), and hunting down drivers after the inevitable fresh install every 6 months. It was a PITA getting the correct driver combos to get my TV add-on card and all games to work properly with my video card driver. I didn't like being told I couldn't run certain software because of the OS version I was using, because the developer wasn't able to account for future versions of the OS and then dropped support for their software (this happened with games as well, such as Wipeout XL). Windows just started to be too much of a pain to maintain.
Then I switched to Fedora, and ran it alongside Windows 2000 for a while. I was blown away that running a program from a console would allow me to see error messages that I could resolve myself. System logs told me everything. Troubleshooting was never so painless. Still, maintaining Fedora was a bit of a pain too, and I frequently fell into RPM hell. There was no streamlined way to update the OS to a newer distro revision without breaking everything, and the desktop just wasn't there yet. Or maybe I wasn't experienced enough.
Anyway, Ubuntu came along and I never looked back. They polished the GUI and went above and beyond to make things as painless as possible for desktop end users, and that really kept me. I still had all the power and flexibility that Linux offered me, if I wanted it. But now it was optional, and the desktop was very painless.
For my gaming fix, I was happy with consoles. I never liked multiplayer much, nor FPSes, RTSes, and CRPGs. I prefer arcade-style games, platformers, racing games, rail shooters, shmups, and third-person shooters. Drop in a disc and go, it's very hassle-free.