Ditching old habits.
Another problem I see is the belief that if something worked a certain way or provided a relatively easy solution on Windows, then it ought to do the same on Linux as well. In a perfect world, this would be great. But these are two very different operating systems. Some Linux purists might even argue that these XP users have had it too easy. That the XP user is unwilling to learn anything new to better understand the Linux way of doing things, should the user wish to adopt a specific distribution. Often, the mindset that purists point to is referred to as a set of really bad Windows habits.
So what sort of poor habits have we become complacent with as Windows users that, frankly, are not going to fly nearly as well on the Linux desktop? Well, to name a few:
Know thy hardware. Without a doubt, the single biggest problem users have is trying to install or configure Linux on hardware built for Windows. It's a tired argument that is as applicable as whining about OS X not installing with a heavy configuration on a PC. The difference is, most Linux distros will install just fine on most common PCs. It is generally on Windows notebooks where users run into trouble with video/audio/wireless, although there are often work-arounds available despite this.
Accept that the software will look different from what you are used to. Because Linux software is often related to either the GNOME or KDE desktop environments that they operate in, often Linux applications will mirror the overall feel of these environments. Problems tend to arise when past XP users become frustrated to discover theyve lost some of the familiarity they once had with Windows after using Linux for any extended period of time.
Package managers are not the same as the old Install-Shield software installation you were once used to. And when trying to install software outside of official software repositories, its not totally unheard of to run into a dependency issue. And more often than not, this leads to frustration as it visually appears that the software installation is at fault based on this problem.
Overcoming potential problems and staying ahead of the curve.
Anyone who considers themselves a power user on the Windows front should not really find migrating all that difficult. The trick is accepting what I like to call 'Linux reality'. Once the user first understands and expects the challenges listed above, they begin the process of learning what works and what doesnt based on their needs, while the rest takes care of itself.
To get the end user started off right, I would recommend the following:
Learn where the provided documentation for your selected distribution is study it before asking for help.
Make yourself known in the forums for your selected distribution after following through above. Also reciprocate with help whenever possible to keep the flow moving forward for everyone.