Moving users to Linux can be tricky, but Jack Wallen has some practical measures that should ease the transition.
Sheer economics are making the use of the Linux operating system increasingly widespread. It is free, reliable and safe. But when adopting any new operating system, users always have a lot to learn.
On top of that, many users think Linux is hard to use, which is, of course, not necessarily true. But it is your job to overcome their reluctance and train them to use Linux so it becomes second nature, and so they are just as at-ease with it as they are with Windows.
Without sending users on some sort of boot camp, changing the preconceptions of users may seem a daunting task. But there are ways to ease the pain of learning Linux.
1. Standardise on a Windows-like desktop
Home is where the heart is, and this applies to the computer desktop as well. There are plenty of Linux desktops to choose from, and the one you select can make or break your users' Linux learning experience.
If your users are PC un-savvy and have used only Windows, make sure you stick with K Desktop Environment (KDE) or Xfce. You could even use a modified Gnome to look and act exactly like the Windows desktop. Take this even further by modifying the default start menu of either Gnome or KDE to parallel the Windows Start menu. Now when your users sit down to their Linux desktop, they will not feel as if they are working in a foreign environment.
2. Get users familiar with applications before you switch
Before you migrate users from Windows to Linux, help them to become familiar with the new applications. Because some of the most often-used applications are cross-platform, you can start them on the applications while working in their familiar environment.
For example, you can start them on OpenOffice and Firefox while they are using Windows. Because they will be doing most of their work in these two applications, by the time they get to Linux they will already have some level of familiarity.
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There is also a port of Evolution — the Linux version of Outlook — for Windows. If your users use Outlook for email and calendaring, using this port could be a positive step in your users' Linux education.
3. Choose the right distribution
Why would you choose Slackware as the distribution for new users? You wouldn't. Slackware is not a distribution aimed at ease of use. But plenty of distributions are available for the novice.
Ubuntu tops the class for ease of use. But Ubuntu is not alone...
Talkback
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Good set of points, here, which can also be applied to your relatives - I've introduced openoffice.org and firefox this way, leading to Linux on at least one more home laptop.
The only problem I can see is that some aspects (dual-booting, test machine, installfest) assume a certain level of interest on the part of the workers, and I know most of my non-techy colleagues wouldn't care enough to make the effort. Here you'd need to plonk the new system in front of them, having made it as straight-forward/familiar as possible, and give hints and lessons as appropriate. Still, slow and steady wins the race!
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I hadn't heard of adept so I followed your link. The developer apparently ceased development in December. That doesn't mean your general advice is wrong but you should revise this section.