Invalid File Name Errors when syncing to Ipod

Question

Ever since an update last fall I have been getting Invalid file name errors when I try to sync my ipod. A window would pop up saying "Windows could not copy 'SONGNAME' to the iPod 'IPODNAME' because an unkown error occurred (-37)." I would press OK and another window would immediately pop up that would say, "Attempting to copy to the disk 'IPODNAME' failed. the file name is invalid or too long."
The windows would keep popping up countless times until the sync would just seem to time out and stop.
The problem songs would have no problem playing in iTunes.
Prior to the update this did not happen. No new songs were added around this time and nothing was changed to my file directory structure. I was too busy to troubleshoot this problem at the time and hoped that another update would fix it. Well, here I am many months and updates later and still no fix. After fiddling with iTunes and resetting my Ipod multiple times (goodbye saved angry bird games)I have found out that:
1. By writing down the file name when the error windows pop up I can get a partial list of the problem file names. I could not get a complete list of the problem files because the sync would time out before a full list could be compiled (the list appears to be in the hundreds).
2. If I changed the name of the file by adding OR deleting one character, remapping the song in itunes, the song would then sync properly.
3. If I changed the name of the file, remapped the location of the file within iTunes, changed the name of the file BACK to the original name that iTunes supposedly had a problem with, and then remapped the location of the song within iTunes, the song would then sync properly
4. If I moved the song to a different directory without changing the file name, remapped the song within iTunes, the song would sync properly.
5. If I moved the song to a different directory without changing the file name, remapped the song within iTunes, moved the file BACK to the original directory, remapped the song again, the song would sync properly.
6. If I renamed the file and then named it back to the original file name WITHOUT remapping the file location in iTunes, the song would still not sync properly
7. If I moved the file into a different directory and then back again without remapping the file location, the song would still not sync properly.
8. Changing or deleting the tags has no effect at all.
9. File name lengths are already under 200 characters and there are no special characters used.
So, to sum up, I have found out a way to fix the issue. The problem is, that there are hundreds of songs that appear to be affected and renaming or moving every single one individually and then remapping is extremely inefficient and ignores the cause of the problem. I also did not want to delete the itunes library and then add all of the songs back in because I have many custom playlists that I have spent hours creating and I do not want to delete them.
Is there a better way to fix the problem? Especially if someone knows the root cause?

Answer 1

I got a procmon log file and examined it. I have the file and I could also provide you with that or screenshots of it.
There is nothing unusual about it. I can see entires in which CR has successfully opened the report and has cached in a c:\windows\temp.
However there is one or two non-successful entries that may be related, especially that examining the stack trace brings us to a call to get_ProductLocaleID():
- A call to read reg entry HKU\S-1-5-20\Software\Business Objects\Suite 12.0\Crystal Reports\Locale fails with NAME NOT FOUND.
- immediately after that and from the same process (w3wp.ex) there is a call to open directory "c:\" which is logged as ACCESS DENIED.
Any subsequent unsuccessful calls seem to be results of exception handling in the debug code.
Does this point to any setup issues with CR? We always run the redistributable x86 runtime when installing it.