Since January of this year (2010), I have helped 3 separate people make the switch over to Linux from Windows. Last year I helped two people do it, and I am currently in the process of converting our desktop (used primarily by Melissa) over to Ubuntu as well. In 2011, I helped 3 other people convert, and also all 3 of my coworkers at my new job.
To date, only one of them went back, but to be fair, I wasn’t able to help him in person, only over the Internet (and being able to play World of Warcraft was a dealbreaker for him — WoW does work, you just have to hoop-jump a bit to do it). UPDATE: I play Skyrim on a regular basis via Wine with little to no difficulty.
My distro of choice, of course, is Ubuntu. The latest release as of this post, Karmic Koala, offers many really awesome features, some of which aren’t even offered on Windows.
The key factor for conversion is quite simple: most people only need some really basic features to be satisfied. If anyone has ever asked you for advice about what computer to buy, if you ask them what they plan on doing it, the answer is often “Oh, you know… email, Internet, pictures, word processing; nothing fancy, I don’t need a gaming computer.”
For the scope of this post, I’ll be discussing Ubuntu exclusively (I’ve found it to be the most accessible for new Linux users and it has a good online community base for support), though many of my sentiments will also apply to other distros (Fedora, Mint, SuSe, Debian, etc).