Comment Why? (Score 5, Insightful) 448
My first question is: Why? Why, if they're both hateful and fearful of change, would they need to change? Why not a newer version of Windows or a Mac?
Users aren't oriented towards their OS, they're oriented towards their tasks. Their typical question will begin with "How do I..." and then continue into "but then how do I...". So your first issue is to determine what they use and how they use it and then find out the best way to solve each of those individual use cases or problems. For example, "How do I manage my finances, I currently use Quicken?" or "How do I upload pictures from my camera?". You need to solve each of those use cases in a sane manner that's easy to use and just as good or better than what they have. Typical users, especially the ones you describe, don't want to spend any more time with their computer than they need to.
Don't underestimate a user's ability to forget things that they do on their computer. Again, they're task-oriented and so they won't necessarily remember that they need a certain program to update some infrequently used spreadsheet twice a year.
Only if you can help them complete their tasks should you switch; you shouldn't switch them to Linux because you perceive it as better; it might not be better for them and then they'll have a tainted view of Linux when in fact the problem was that they couldn't use their silly banner-creation software from 1999 on it.