iPod Video (5th Gen) Won't Transfer Songs

I have a 5th Generation iPod (black iPod Video) which, according to the listing of supported iPods with the iPod Device Support add-on, is designed to work with Songbird. I've tried dozens of times to transfer songs from my Songbird library to my iPod, and it gives me the 'syncing' message, and says it is successful, but none of the songs actually appear in my iPod library. I've done all the updates I can, changed all the settings I can, I completely removed iTunes and have done everything I can find online to make it work.

Why doesn't it work?

Thanks for your help.