IPod frozen and iTunes freezes when resetting

My iPod and iTunes are acting up. iTunes froze when I tried to update my iPod. Then my iPod was locked in Do Not Disconnect state. Forced restarts many times to get it running, so I started the reset process. When I try syncing with iTunes to put everything back in it hangs on a podcast and the cycles resumes. I've managed to get into the diagnostic mode and it tests out OK. Is it iTunes or the iPod?
It's a click wheel model before the photo version was released.

Got it working again, but I've only tried putting a few songs back on it. The auto process kept hanging. Listening to a new album I bought and it keeps skipping within songs. It doesn't always do it, and if I go back and listen to the skipped song it plays fine. Though once it wouldn't go back and I had to force it to restart.

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    The select button + menu button thing worked, I just realized that when I was trying it before the hold was still on (since I was "toggling it"). I feel stupid...

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