Several years ago my wife was using Hoary Hedghog on her laptop and it suited her just fine, but I really haven't tried switching family members away from Windows to Linux. Actually I have counseled them to get Mac's but they haven't gone for it.
But this week my sister in law got some nasty malware from Facebook (this appears to be going around) and spending a few hours descending into safemode trying to get rid of of it with McAfee, Windows Defender, and ClavAV. No luck. Yesterday I had booted up with a Fedora 10 LiveCD and my brother liked the look of that and given the hell of dealing with malware they are willing to give Ubuntu a shot. They already use OpenOffice and Firefox sould it is the ideal case. But we'll see if it is painless enough.
So I added Ubuntu 8.10 to the Dell Optiplex 330. Added medibuntu repos, installed flash, Realplayer, and the codecs for mp3's even added the Gnome weather applet to the toolbar. Hell, even imported their pictures into F-Spot. What I was most pleased about what that the several year old D-Link PCI Wireless card worked out of the box, even with WPA.
What didn't work well was the GUI partition resizing, which failed silently, but I was able to drop down and do an ntfsresize -i to see that it was unclean NTFS partition.
So there is no way that an average user could do Dual Boot or setup all the repos and install the software themselves without doing a whole of lot of reading, but now we will see how painful it is. I'm particularly concerned about printing. My sister in law still needs access to some windows programs so I'll try Dual Booting and/or possibly VMWare Player.
If this is successful I want to replace XP Home on my mom's 3-4 year old Dell laptop because it is starting to die a slow death.