Stumped! Help!

So, I recently bought a 120G iPod classic from a reliable guy. For the first couple weeks, it worked pretty decent. There were a few flaws, like being unable to add new songs without restoring the whole iPod, and a window that kept popping up asking if I would like to fix some files on the device. Even if I clicked yes, the files would never restore, so I ended up clicking cancel for the majority of the time.
Last week, however, I upgraded to the new version of iTunes. Unfortunately, with that, my ipod was no longer able to sync or restore itself. Along with that, whenever I even plug my device in, The whole system freezes until I unplug it.
I have tried everything. Different versions of iTunes, contacting the previous owner, googling help, and anything I could possibly come up with, but nonetheless, nothing has worked.
I would really appreciate it if someone could help me out here. I leave for a flight next week and I would really like to take my iPod along.
Thank you!

Sounds more of a software issue. Especially the bit about starting up in safe mode. I have seen all sorts of odd issues from CS3 installs, mostly on Intel machines though. So here is a random thought. Go to your /library/receipts folder and delete any safari related files. This will cause the OS to re-download any safari updates when you run Software updater. Now go to Software updater and get all safari updates again. My thinking is that re-running the updates after CS3 is installed will fix any damage CS3 did (if any). This is just a guess from experience with CS3 install issues. Also check adobe's website for CS3 install issues would be good.
I don't recognize this as a hardware issue. I think it is a software bug.

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