Will he switch? When I got my new AMD Thunderbird in January, 2001, I finally made the leap from the Microsoft Windows world to a Free Operating System. My OS of choice was FreeBSD: a modern open source operating system that is extremely stable. Unfortunately, FreeBSD is designed primarily with servers in mind. I could do everything I wanted to with FreeBSD; unfortunately, it usually required navigating cryptic config files and compiling something many times. Finally, in August, 2001, I followed my roommates and switched to RedHat Linux. GUI installation and configuration! Unfortunately, despite the vaunted RPM system, installing new software is still not incredibly easy, but it's better. Slowly, I'm working my new system into just the way that I like it.
In August, 2003, I got a new laptop computer, an Acer Tablet PC. Read below for my adventures installing Red Hat 9 on it!
In October, 2004, I got a new Dell desktop computer. Fedora Core 3 installed on it with almost no effort. In November, 2005 I upgraded my desktop to Fedora Core 4. This was also painless.
In December, 2007, I upgraded my laptop and desktop to Fedora Core 6. There were no problems specific to my hardware (though not installing the right kernel for i686 computers?! Come on!).