My parents currently use Windows ME (believe it or not) on a fairly old computer. According to them, their computer crashes quite often, which is not a surprise at all. In fact, I'm surprised it's still in a usable state.
The only thing that would have prevented them from using Linux before is that they use a windows only genealogy program called Personal Ancestral File. They wouldn't be willing to learn a new program like Gramps to switch to Linux. They're not very good with technology, and any program switches would just confuse them. The rest of the OS could be setup to be very similar to theirs.
I've tried installing PAF 5 in wine on quite a few occasions without a lot of luck. I would usually get some things that worked, and others that didn't. Plus the setup of wine was usually just a pain in the butt.
Since Ubuntu 7.10 worked so well for my printer, scanner, and pretty much everything else, I decided to try and install PAF again.
First, I had to of course install wine, which was a simple selection in add remove applications. Then, once I had downloaded the .exe installer for PAF5, from the command line I just type "wine PAF5EnglishSetup.exe". Do this from your regular user account, or it will be installed in root's directory and you won't be able to run it. A shortcut is automatically added to the menu after the install is finished, and everything is ready to go. (yes, it's that simple)
Next time I'm visiting them, you can be damn sure I'll be installing Unbuntu 7.10 on their computer!