Having the perspective of using DOS and OS/2 way back when, every iteration of MS Windows past 3.1 has left me with the nagging feelings; "It shouldn't be this hard" and "An OS could and should run so much simpler/easier/smoother/lighter than this."
Unless super-bored, I've never been a cutting-edge type person. I don't upgrade until I have to. I let others iron out the kinks and I use what works, even if it's old. Tinkering and troubleshooting is fun if I have the time to play, but it really pisses me off when I need & expect something to work and it doesn't.
When MS announced it was dropping XP support, that was the straw for me and I started shopping for an alternative. (I was so very sick of my XP installs tanking after about 6-12 months, hanging on mup.sys when I tried to boot. It was almost predictable. The silver lining is it taught me good data backup and recovery skills, as well as how to make images and restore systems. Thanks, microsoft!)
I tried linux of some form or another (can't remember) back in 2000, but I wasn't savvy enough (or ready to dedicate the time necessary) to get it.
Today, though, with Linux Mint giving me an out-of-the-box OS that the whole family can immediately sit down and use... WOW! Awesome. And not only does it WORK, but I can tinker and play as I go and grow into it.
And I know that, worst-case-scenerio, I'm 30 minutes away from a fresh install that will, upon completion, be UP TO DATE! And it will include office productivity, printer/scanner/network drivers, a decent browser, and pretty much anything else I'll need. I won't have to spend half a day hunting around, popping discs in and out of the tray and installing optical burning software, graphics & audio card drivers, etc etc etc. yay linux mint!