One word: Don't. (Score 1)

Having been down this road many, many times in the past years, I have but one word: don't. If the person has never used a Windows machine, they'll be completely flummoxed before the end of their first attempts to send an email. And, while I can highly recommend Ubuntu as a reasonable and easily usable alternative, I find myself echoing more the person who sent their grandmother an iMac. That's the way to go, if you can afford it. If not, definitely go Ubuntu. Windows XP and/or Vista will simply drive a user crazy with all of the popups. And nothing is truly automatic on Windows. Imagine getting this message: "Windows needs to install critical updates on your system. Click here." And then they click. And it loads the Microsoft internets and all of the "Hey, we're going to pop up a square box and gray out everything you want to click on just to tell you you should try Microsoft Office". I'm a former IT worker and spend 8 hours a day in front of computers and I have difficulty navigating Vista without putting a fist through the monitor. Think of how the same experience will feel to someone who already feels ignorant. I'd predict this is what will happen, as it is what happened to an elderly friend of mine: The CD tray will get used as a coaster to keep the coffee cup out of the way of the old manual typewriter he's propped up in front of the monitor -- on which the "Aquarium" Screensaver is permanently set.