Help!....I'm going nutz! I can't sync......

Question

This has been an ongoing problem. First some facts:
Computer: MacPro tower, 2 x 2.8 GHz Quad-Core Intel Xeon
Memory: 2 GB 800 MHz DDR2 FB-DIMM
OS: 10.5.8
iTunes: 9.2.1
iPod: 5th gen, 60 gig, ver 1.3
Software Update says everything is up to date.
Previously, I could not even get the iPod to show up in iTunes. This was after a long extended period of no syncing attempts as I was happy with things as they were. At the time, I was running the version of iTunes just previous to 9.2. When I finally decided to add some more tunes, I tried syncing and nothing. 'Couldn't even get the iPod to show up. Neither mine or my wife's 4th gen Nano. I forget the order things happened in, but after a long call (3+ hours) with Apple, we tried a bunch of things including a complete and comprehensive uninstall of iTunes and installing from the Apple website 9.2 (latest at the time). We finally got the iPod to show up on the desktop and in iTunes, but when it tried to sync, nada. Just the spinning beach ball. And if I walked away and left it running (as some have suggested), it would eventually just show a bunch of error messages. Sometimes it would add one or two or three songs then hang. Sometimes it would hang trying the first. And waiting did no good. Both iPods. In desparation, I went a bought a brand new iPod and tried syncing it as well. No luck. I'd tried Restore on both iPods and the process started, then hung as well, and completely buggered the iPods. My wife was leaving on a long trip the next morning and that's why I bought a new iPod. We finally synced her iPod to her MacBook and all was well, even though it was a much older music library.
A few days later, as I was fooling with things again, I decided to upgrade all the software that the updater program said I had to do. This was a bunch of things other than iTunes as I'd already upgraded that in the earlier attempt. I then tried syncing my 5th gen and wonder of wonders, it synced. Same with the old Nano my wife left behind. I thought all was well, but no.....
A few weeks later I went to sync and add new tunes to my 5th gen and no luck. Same problems as before. I ran the software updater and updated all it said to (not much) and still no luck. Then yesterday, after a month or two, I decided to tackle the problem again. This time I noticed that there was a 9.2.1 upgrade. So, I went to the Apple download site, downloaded it, and installed it. Still no luck. I then searched the web and my own brain for things to try. Here's a partial list:
I completely uninstalled 9.2.1, got rid of AppleMoblieDeviceSupport.pkg, got rid of AppleMobileDevice.kext, restarted, emptied trash, restarted, and then completely reinstalled 9.2.1. No help.
I tried syncing with the computer rebooted in Safe Mode. No luck.
I tried syncing with the computer AND iTunes in safe mode. No luck.
I've run the disk utility and checked for and repair any Permissions errors. There were a few but mostly printer related. None that seemed related to iTunes.
I checked permissions on all my iTunes folders as well as on the iPod.
I've tried different USB ports and tried using a powered USB hub as well. No help on all of these.
I finally got my 5th gen to sync by removing all the stuff that I'd tried to add before (the stuff it was trying to add and got hung up on.) Finally, when the library matched the contents of the iPod, it says it synced. Then i tried adding one album. No go. And it didn't matter whether I dragged and dropped from my other internal drive, used the Add to Library function, or imported a new CD. Nothing would sync. Then I tried removing some existing songs. I deleted them from both the library and the music folder. Then sync was successful and the songs were deleted from the iPod. But, when I tried to add the very same songs back onto the iPod, it wouldn't work. It's driving my nutz!
Here are some of the many error messages I eventually get. Some appear if I just let iTunes sit long enough trying to sync. Other pop up when iTunes freezes up trying to sync and I just unplug my iPod in order to unfreeze iTunes. At these times, Quit, Force Quit, etc. does not work.
The various messages:
Attempting to copy to the disk "Martin's iPod" failed. You do not have enough access privileges for this operation. OK.
The iPod "Martin's iPod" cannot be synced. The disk could not be read from or written to. OK.
iTunes could not copy "Love Me Do" to the iPod "Martin's iPod" because an unknown error occurred (-5000).
The iPod "Martin's iPod" cannot be synced. The required file is in use. OK
The iPod "Martin's iPod" cannot be synced. The required file cannot be found. OK
iTunes cannot read the contents of the iPod "Martin's iPod". Go to the Summary tab in iPod preferences and click Restore to restore his iPod to factory settings. OK
I even was able to change the iPod to work as a hard drive and when I tried to copy a jpg or Simple Text file to it, it gave me this error message:
The Finder cannot complete the operation because some data in "IMGP2082.jpg" could not be read or written. (Error Code -36) OK
So, I'm at my wit's end. If you folks can't help me, I'll just have to haul the darn computer and iPod down to the Mac store and have them solve it for me. Fortunately, I have the 3 year plan.
But I'd prefer not to have to do this.
Thanks for any and all suggestions.

Answer 1

Bump......
Nobody has any ideas?? Apple people??