Sad iPod :( -- Please Help!

[udmtree]

My 20GB iPod is having some issues. I have restored it numerous times and run virus scans on my computer. When I plug my iPod into iTunes, it will not copy all of my music -- it will error. Sometimes, the "AutoPlay" window pops up when I launch iTunes with my iPod plugged into my computer. And, when I went to test my iPod by playing a song, it erased and reset. What is wrong with my iPod?

Please help!!!