Windows to Linux

How would you go about converting someone from Windows to Linux? Or, if you have already done so, how did you do it, and how were the results? After running various Linux versions for a few months now, I am ready to start moving my partner, my brother, and various friends and neighbors who depend on me for support to Linux. The question is, how to make that transition as smooth as possible?

Is it worthwhile to switch them to Firefox, Thunderbird and/or OpenOffice.org, while they are still on Windows, in order to smooth the transition, both for them and for their data? I have the full spectrum on this front, as my partner has been using Firefox and Thunderbird for quite some time now, and has used OpenOffice occasionally, whereas my brother has never used any of them, although he recently tried Firefox and wasn't pleased with the way it took over his bookmarks from IE (not a good omen, I know). The friends and neighbors fall between those two extremes.

Should I convert them by setting up their computers to dual-boot Windows and Linux, so they have an "emergency retreat" avenue, if we find something they absolutely have to still use Windows for? Or given that disk prices are cheap these days, should I just buy each of them a new disk, and load it with only Linux, keeping the Windows disk in reserve "just in case"? Or perhaps I should just make them go "cold turkey", and convert their existing disks entirely to Linux? Or has anyone had really worthwhile experience by first running one of the Live CD (or Live USB) distributions first, and then taking the plunge to conversion? I suppose this might at least reassure the user about the viability of Linux, but it seems like an unnecessary extra step to me.

Any other recommendations, tips, pitfalls, experiences or war stories would be appreciated.

After gathering some opinions and recommendations, I'll start with a few of the closest systems, and see how it goes.

jw 4/9/2008