When connected via USB, my Ipod Classic 160GB mounts as a disc drive, then changes to a white drive. When iTunes automatically opens, it crashes trying to mount and/ or sync. When it times out, my only choice is to restore, but that doesn't fix problem.

Question

I'm running OS 10.6.8 on my 3.06 GHz iMac Intel Core 2 Duo.   I recently upgraded to iTunes 10.5.2.  I'm not sure when the trouble started but I attempted a restore when the iPod would not play correctly.  It would start to play a file and get stuck on 0 seconds.  If I put the iPod on shufle, it will stall on 0 seconds for 15 seconds or so and then move on to the next track and stall again and so on.   Seemingly randomly, it will play a few tracks but eventually start skipping again.  This will continue until the battery is depleted which is fairly quick since the drive is constantly spinning.
My 160GB iPod Classic after restore attempts now is up to date with 2.0.4. and of course, nothing works as it should and I would say the skipping issue is worse than ever.  
When I connect with any of three USB connectors, the iPod mounts to the desktop as a grey/silver disk drive picon exactly like the Macintosh HD picon.   Then Finder will stall for a few minutes- spinning pinwheel.  Somehow, the dock is never affected and I am able to open other applications like Safari or tab through open windows- just no action on the desktop.  Eventually, iTunes automatically opens and Finder becomes responsive again.  At this point the grey drive picon on the desktop becomes a white drive mount picon, but the iPod does not mount in iTunes, yet.  At some point, the iPod attempts to sync, iTunes crashes with the spinning pinwheel and eventually times out and I am prompted to restore the iPod again.  Once restored,  the iPod properly mounts under devices in iTunes and, as I have done this several times, even occasionally changes to the regular iPod picon on the desktop.
I have restored several times going as far a completely deleting iTunes from my iMac, downloading the latest directly from Apple.com, and attempting to restore again, but to no avail.
I have even used the disk utility to verify and/or repair my Macintosh HD and iPod. 
It seems lots of folks are going through this ordeal.  Has anyone had any success in fixing the issue, even if only temporarily?

Answer 1

one more detail, after a restore, when I attempt to reload music to the ipod, if I try and move, say, 20 files, the transfer seems to work as it should but then stalls on the last file.  Eventually, the status will change to "Updates Files on (my ipod)" a and suggests the iPod is syncing  even though I have the auto sync feature turned off.
This process eventually works itself out, and seems to take longer relative to the number of files I attempt to transfer.   Once done, howver, if I try and eject and dismount the iPod, iTunes stalls with the spinning pinwheel and I am warned that the iPod is syncing again with the spinning candy cane status bar.     Eventually thisd works itself out and the iPod dismounts from iTunes and the desktop and eventually the iPod is free to disconnect.
Then if I try and play the music I just transfered, the iPod says there is no music loaded.
Ideas?