Win2K Pro was a godsend after using Win98 for a few years. To go from something that would randomly bluescreen and couldn't be trusted to run longer than 2-3 days tops, to something that I almost couldn't crash it if I TRIED... was a great feeling. I would hear people claim it "wasn't good for games" but I honestly never had any trouble running anything. In the remote cases where something was unresponsive, the ability to just force-quit and relaunch the Explorer shell without rebooting was great.
Around 2006 I was forced into using XP as the video card driver support for 2K became unreliable, but at least by then the power of PCs was such that you could just beast through the bloat of the OS, so it wasn't as much of a liability as it was when it first came out in 2001.
IMHO Win7 is actually a very respectable OS. It's the first one I bought on my own since building my first Windows box in 1998 (which I got at OEM pricing). I can't see any viable reason to upgrade from Win7 in a desktop environment for the forseeable future. And even if/when I do buy a tablet, it still sounds very immature and worth waiting 1-2 years for them to get the kinks out. Especially with how nice I hear Jelly Bean is for Android tablets.
Any home user with a modern system still clinging to XP is a Luddite IMHO.