Thanks for the question, and great troubleshooting so far! iPod software version 2.0.5 is available for the iPod classic 160GB (Late 2009). If this is your model, you may want to update the iPod. If you are having issues with your iPod, the following troubleshooting assistant may help:
Additionally, you may want to check out these articles:
Thank you Matt for trying to help me on this issue---on Itunes when I check for updates for the firmware 2.0.4 it says that there are none available. How do I update my ipod outside of itunes? I've tried all of the resetting steps for my Ipod provided with no sucess so far. My ipod is being recognized in itunes and windows the device just doesn't sync my purchased songs to my Ipod from Itunes. When I go to the Help tab in Itunes everything is just fine until the Device Sync Test - Itunes says Ipod not found. Hopefully I don't need to go visit a store to resolve this issue. Also, when I attempted to load a CD in Itunes, the program stopped working after just one song. Any more help you can give me would be greatly appreciated.