I NEED help. Ran out of ideas.

I have 2 problems with the same Ipod.
The Ipod is an older model, monocolor screen, a click wheel. The ipod is currently formatted in Windows.
Now here's my problem, whenever I try to play a song it automatically skips it. The song title, and everything else comes up but the play timer stays at 0:00 and it just skips it, and then skips the next one, and the next one, and so on.
So, I tried everything i maunlly could to it and nothing worked. So then I decided to just plug it into my MacBook and restore it, and re-format it to Mac instead of Windows. But here is the second problem: Whenever I plug it in to my notebook, the ipod says "do not disconnect, and it comes up on my desktop, and then itunes pops up like it found the new device, but it doesn't show the ipod.
I have tried two things:
1. I ran the "software update"
2. I have updated Itunes to 7.1.1
Also, I ran the program alterPOD and even that found the program. But when I attempt to use the iSYNC it can't locate the ipod.
I have seriously ran out of ideas for both of the problems.
MacBook   Mac OS X (10.4.9)   1.83GHz Intel Core Duo, 512MB RAM

have you tried restoring the ipod?
Restoring iPod to factory settings

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