Hey gabeckmeyer!
First, go to your iPod on "Settings > EQ". What is your EQ set for? If it's a specific sound setting, then try switching it to "Off". If it's already off, experiment around changing it from "Voice", to another option.
This may work for you, as switching around with the EQ settings has done for others whose iPod's restart or skip.
In iTunes, go to "Help > About iTunes". What version are you running? 7.0 or 7.0.1?
If you aren't upgraded to 7.0.1, I would first suggest to try that. Download it here ->
iTunes 7.0.1
After installing 7.0.1 (if you don't already have it), then be sure that your iPod's formware is updated to the latest version. Do that by:
1 - Connect your iPod.
2 - Click on your iPod in the left-source panel.
3 - Under the "Summary" tab (you should be on there anyway), see if your iPod is up-to-date or not. If it isn't, I would suggest upgrading to the latest version of firmware, and see what that does for you.
-Kylene
If any post helps or solves your issue, please mark it that way accordingly. Thank you for helping the boards!