iTunes really works great with the iPods, even if you don't use an iPod it works great just for organizing your tunes.
Make yourself a couple of play lists. Drag and drop only the songs you want to listen too. Although 8GB is not that much it should work great for just using a few play lists on the bike.
My iTunes file currently has 46GB of music on it, but only half of that is downloaded to my iPod video.
And I will be adjusting my list a little more, I plan on replacing the video version with an iPod touch 64GB.
The problem with the video is they are hard drive based and tend to lock up with too many bumps in a row.
BTW Sony has a new radio with a internal tray for an iPod, works pretty good.