Why won't my iPod touch sync with iTunes?

I recently bought a new song and wanted to put it on my iPod.  Every time I went to sync it "timed out" and wouldn't show up on my iPod (ie the sync failed).  I tried updating iTunes.  My iPod won't get any new updates since its 2nd generation.  I've tried the diagnostics and everything checks out okay there.  My computer is up to date.  I thought I'd try to do a restore and now I have less songs and none of my apps.  It's now getting "stuck" on other songs from my collection.  Any help?

Okay, so I think it may be the cable b/c when I hold it just right it works much better.  It still will get stuck on certain songs but when I try again it works.

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