Bountyhunter...I've had the same problem you have. Lost everything when I synched the first time, years of music that was only going to be copied onto my ipod. Luckily I had backups. The software and the ipod is not at all user friendly and is not at all like any other software I've used. I smashed the little thing in my vice and mailed it back to them. I will never buy another apple product.
Bought a creative labs zen xtra and I've never been happier. Sounds like you've solved your problem so good luck.