In 1999, I gave up on MS Windows entirely and actually purchased Redhat Linux. I went through a couple versions of the kernel, and learned alot about how to run the OS. It did pretty much everything Windows did, but never easily. I was searching for something more polished, and easier to use and I decided to go with the MAC iBook and OS X. I was so happy with it that I gave away my old desktop to the lady across the street leaving myself no PC to run linux on. My wife has a Dell and I threw an extra hard drive in it, but OS X did everything I needed, so I never bothered to "borgify" it.
Recently, a friend at work turned me on to the latest distro of Mandrake Linux (9.2) which he had downloaded and burned onto two CDs. Holy Cow. What a difference from Linux distros of old! I think we're finally approaching a Linux that you could install for Grandma and not frighten her (too much). My wife's machine is a Dell Dimension 4100 (PIII 800) with an HP scanner and an HP deskjet (previously never worked with Linux). I was able to get both of these devices working with no problem. The cool thing is that now the printer is shared (using CUPS) and I can print from the iBook which I could NOT do before! I set up shares (using Samba) so the iBook and the Dell laptop can share files with the Dimension which has a huge hard drive. The only hiccup was the lousy winmodem in the Dell, but since we don't use a modem now, I can wait to mess with that.
The pokey old desktop has now been turned into a real server too which is a big difference from when it was running Windows. Now its a web server (with mysql and php installed) so I can dump all our family photos there and point family and friends to our (minimally changing) IP address. I can get in via SSH and run a VNC client and control the desktop from work or the iBook. It has a full install of the Gimp (photoshop), Open Office which for all intents and purposes now is even better than MS Office. The Palm Pilot synced with no problem (had to set a sim link to /dev/pilot, but I could do that for Grandma).
All in all, I'm very impressed. I feel pretty confident that if you have an old PC and you want to set it up for Grandma WITHOUT buying Windows, you could do so using Linux now and she might not even be able to tell the difference. You could set her up so that you could access her desktop remotely to fix whatever issues crop up, and you could rest assured that it won't crash on her when she's trying to do something the wrong way. All around great distro!
You can download the latest ISO images (to burn onto a CD) of Mandrake here [link dead 2024
].
There are a bunch of screenshots on their features page [link dead 2024
].
update 2024 - this site was later archived as https://www.mandrakelinux.org/