I tend to use Amarok, one of KDE's most popular audio players, to manage my music. Amarok can usually handle synchronizing music on an iPod just fine, but it turns out that it doesn't play very well with my 3-gen iPod nano. For one reason or another, any time I tried to copy music from my linux box using Amarok, the whole iPod became useless. The device recognized that space was being used, but it wasn't recognizing any music or movies or anything. Because of this, I have been using my wife's macbook for the past while to synchronize my iPod. It's been working fine, but it sure is inconvenient to interrupt her when she needs to be doing homework or something and I want to pop into iTunes for a few minutes.
Today I was listening to my iPod and doing some homework between classes when all of the sudden my music stopped playing. I thought the playlist might have ended, so I went to start the music up again only to find out that the little guy had locked up (it does this from time to time). I couldn't remember the reboot sequence off the top of my head, so I Googled it and stumbled across a short and sweet article with the goods.
This article also referenced the use of a program called Floola in place of iTunes. I decided to investigate it briefly because my homework was boring me. Come to find out that Floola is free, works on Windows, Linux, and MacOS, and it actually does support my 3-gen nano! It also has some cool features like being able to download music videos straight from YouTube and converting them to work on the iPod. I'm really enjoying the program! One less reason to keep Windows around!