DOS was my first mainstream OS and Windows 3.1 was the logical next step. Win 98 Plus was terrible, and prompted me switch to Linux. I wiped the hard drive and went through Red Hat, Fedora and finally settled on Ubuntu. I realized early on that I needed Windows to get some basic stuff done, even though Linux was great for programming due to the atrocious driver support. I went dual-boot through XP and Vista. I am not a huge gaming addict, but I do indulge in multiplayer RTS from time to time and the occasional FPS bout. The dual boot solution worked great for this. I am a command-line first person (you can do everything in Emacs), but not all applications can be effectively used with only the command line and this is where the GUI comes into play.
I was familiar with the basic windowing environment through Windows and Gnome and it worked fine for all intents and purposes. I was given a Mac at work, but the very notion of having the current application take over a portion of the static OS taskbar was very hard to get beyong. Besides, the drawbacks of fewer software and the steep prices along with the hardware changes (see the one button mouse) kept the Mac out of the house and it was soon off my desk at work too.
I dabbled with Solaris (with Gnome) and found the experience mostly positive. Ubuntu was great since it ran most of the apps I needed and I had open source alternatives to the ones it didn't. However, my schedule required me to work from multiple places in a single day and dual booting off a laptop and switching OSes became cumbersome. Windows 7 came out at the same time and it was a many fold improvement over Vista. The UI was familiar yet cleaner and snappier. Bolted on to an Intel i7 chip, it was quick and very stable (no BSODs in 3 years of running). I am now running Ubuntu in a VirtualBox but may consider moving to Mint since I am not a big fan of Unity. (Windows 7 guest on a Ubuntu host was not stable).
I like what I have seen of the Windows 8 previews so far and unless there is an alternative that can run the applications I need with good driver support in my price range, I don't see myself switching.