
My parents got their first relatively modern computer in early 1996, a Compaq Presario with something like a Pentium 75 and a 1.1 gig hard drive, running Windows 95. My Dad to this day has not been bitten by the Internet bug, but Mom most definitely has. During the six years I spent on the other side of the country, I'd say that more communication between myself and home took place via instant messenger and email than did by phone. She cut her teeth on that Windows 95 system, and in 1999 it was replaced with a nice Dell Pentium III running Windows 98.
One new hard drive, OS reinstall, and a failing DVD-ROM drive later, that computer is still running Windows 98, with only one log-in. It's true that Win98 did implement a half-assed sort of user management arrangement, but it was always my impression that it caused more problems than it solved.
So, one user account on the computer whether it's Mom (which, 99% of the time, it is) or myself or one of my siblings checking email or doing a bit of surfing while visiting the homestead. That means that my poor Mom inherits the after effects of every single OS/software configuration tweak or application experimentally installed by one of us... document types that used to open in one application will suddenly open in a new, unfamiliar one, or not at all. Things behave just *slightly* different, and since nobody really documents what they changed when, it's hard to put everything back the way it was.
Anyone who's owned a computer for an extended period of time knows what it's like to have everything just so, only to have something like the RealPlayer installer come along and take over all of your file type associations, and install 18 different apps that all run in your system tray. It's damned annoying!
Since returning to the east coast I often find myself fielding the tech support IMs resulting from these issues, and I've adopted a very hands-off approach to Mom's computer. I touch no control panels, no preference panes, and install no software unless it's warranted by the troubleshooting I might be doing.
I am hesitant to recommend that my parents upgrade to Windows XP (especially with the $200+ price tag for a new license), but I know it would make a lot of these issues go away if my brother, my sister, and I each had our own accounts and preferences that were completely compartmentalized from my parents'. I use my PowerBook conspicuously and talk up Mac OS X at every opportunity when my parents are around and the subject of computers comes up, and if I get wind that my parents are thinking of buying a new computer I'll go into car salesman mode if it means I might get them to switch... so many little obstacles and annoyances that come from day to day Windows usage by non-power users like my folks would just go away in OS X.