Migrating Silver-Surfers with minimal computer skills from Windows to Mac
Solution 1:
You could try leaving them with a copy of the relevant books from the Missing Manuals series. I helped my parents switch to a Mac a few years ago, and bought them the Tiger and iPhoto books which they've told me have been useful.
This will depend, of course, on whether or not they're the kind of people who would be willing to read documentation of any sort. (I'm not sure my own parents are, which makes me suspect they're only humoring me. ;))
Solution 2:
I have migrated my wife's parents to Mac OS X. All they want to do is surf the web (including online banking), read e-mail and play some card games. By Putting all of the necessary icons in the dock, they are perfectly happy. They have often said that the "new computer" is so much easier than the old one.
P.S. Install TeamViewer http://www.teamviewer.com for super easy remote access so you can help them out when necessary
Solution 3:
If they share documents with others they'll have to learn about file formats and interoperability.
My Dad's Windows computer died a few months back, so I lent him my iBook G4 to use while he waited for a replacement. He shares files (mostly word processing documents) with other people "of a certain age" as part of the work he does for a non-profit in his spare time.
These people come from hugely varying levels of experience with computers, and as a group they just don't get the idea of file formats. Trying to educate everyone and force the team onto a standardized format could be, well, difficult to put it mildly. Some people send files in Word 97-2003 format, some in ODF, some in DOCX, one even in TXT.
When my Dad was using Office 2007 on windows, this was no problem, but the shift to Mac Office mean he had to spend a lot of brain cycles on unreadable files, or files that don't convert perfectly.
After a month he had re-named Apple to "Crapple" and he swore of Macs for life.