When I plug in iPod - iTunes crashes?

Hello.. sorry if this is a repeat question. I lost track of my user i.d. and couldn't track down my question. Anyways, when I plug in my ipod - iTunes loads as usual. However, it crashes and says "this application has failed" or something like that. Usually, my ipod would say "ipod is updating". Now it just sticks with "do not disconnect". My actual files are all still in the ipod - files and the songs are still in itunes. But when i look at the music directory in my ipod - it's empty (due to the no updating thing). It's driving me crazy. I've tried a couple of earlier suggestions and they didn't work. I've uninstalled itunes and re-installed it and that didn't work. I was hoping i wouldn't have to reformat my ipod but if that's what it will take I guess that's that. Thank you very much in advance for any suggestions!
-chizg
p.s. off topic I know, but since I have your attn.. I have a bigger problem too. All my files (college work for a portfolio!) were dragged in the trash and i hit "empty trash" - so now I'm screwed. I know trash isn't truly trashed so if anybody knows the step by step process on how to recover it I'd be grateful. Thank you for reading.

Hello. The message was:
"The application iTunes has unexpectedly quit. The system and other applications have not been affected."
I haven't gotten around to trying the link out yet becuase I'm still scannning it for my deleted files. Thank you for any other additional help regarding my ipod/itunes issue.

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