Why doesn't the iPod classic sync properly, and how do I fix it?

Notes
Before anyone mentions the lame suggestion of "Restoring", let me add that I have done that. Alot.
I'm pretty good with computers, so please get as nerdy as you want, just as long as you're only trying to help me.
This disscussion should only be about this particular problem, please refrain from posting you're problems to this (Make your own discussion).
If necessary, contact me via email if you need more information, or have other misc. questions or inqueries.
Basic Information
Product: iPod classic
Serial Number: ******0YMV
Model: MB147LL
Version: 1.1.2 PC
Capacity: 80GB
Diagnostics
Retracts: 14
RealLocs: 4928
Pending Sectors: 120
PowerOn Hours: 443
Start/Stops: 16585
Temp: Current - 31c
Temp: Min - 3c
Temp: Max - 67c
Additional Details
The iPod works fine after immediate restoration, however, after adding 500 or so songs it seems to quit responding and appears to terminate communications with computer while freezing iTunes. After fiddling around I usually grow tired and unplug it and iTunes quickly displays a message saying to restore the iPod, although it's unplugged... This happens everytime, so it's not a rare situation for me. I've tried repeatedly on two Windows computers and a brand new Mac.

It is hit or miss whether replacing the cameras will resolve the problem. I would first try taking it apart and then carefully disconnecting and reconnecting the camera cables.
Since it both cameras it is likely not a problem with the logic board but still could be.

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