Robert Movin over at TidBITS has a nice little article that I expect many of us can identify with. After years of being tech support for his mother (and other family members), he got fed up trying to remotely support her aging PC and decided to take the plunge and get her a Mac. He describes the how he set it up for her, including using VNC to allow him to remotely control it (I'm not sure why he installed OSXvnc when OS X has a built in VNC server, however). He also discusses some security issues like using VNC over SSH, and how to deal with her dynamic IP address.
So what are your experiences with setting up Macs for less tech savvy family members? Have you found any particularly good tools or techniques?