Ipod emergency!

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U2isthebest

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So I went to plug my iPod in this morning and it's not syncing. It's charging, but I'm not getting the "Do Not Disconnect" symbol or the syncing page to come up on iTunes. Also when I unplug it, my iPod still has that little black pin through the green batter symbol in the upper right corner like it does when it's still charging. Does anyone know what's wrong?
 
The same thing happened to my dad. They told him it might be the connector might be broken and that since it's out of warranty, he would need to pay 100 dollars to fix it.
 
That's happened to me before--I reset it and then restored it to factory conditions, and then re-sync'd it.
 
At first I thought my 5thG video was just on it's last leg, but I'm beginning to think it's an iTunes issue. I've been having the same problem. Sometimes it won't sync, sometimes it removes all my music and then re-syncs (takes forever..), and sometimes I get an error message saying my itunes library couldn't be saved. A restore usually does the trick if nothing else will. I wanna buy a new one, but I'm trying to hold out to see the latest releases.
 
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