iTunes library consolidation error: "Copying files failed. An unknown error occurred (-50)."

Just trying to give this topic a poke as I am having a similar issue.

I am rebuilding my library that was on an external drive. I had a backup of much of the files, but not a direct backup of the iTunes media folder, as well I am now moving it to a new iTunes Media directory on a Synology 1813+ NAS running DSM 4.3 vs. a USB attached drive.

I have followed all of the correct procedures to move the media directory by using the tools within iTunes, and that all worked perfectly.

So far iTunes has been able to locate most of the music files through its own processes. Once it completed that process I then initiated "Consolidate files" to move the found files to the new iTunes Media directory on the new NAS.

I am led to believe that the issue is with a specific file that causes the copy process to stop, but I don't know how to capture what file it might be.

I am not seeing anything relevent in the console log.

Hoping someone can throw me some ideas...

iTunes 11.1.2 (32) - iMac 2.8GHz Intel Core 2 Duo 4GB RAM - OS X 10.8.5

Not sure whether you found a solution but after having the same problem I found a way of finding the file causing the problem (in my case a podcast with a very long file name!). You can find the solution in on this thread (1st reply)

https://discussions.apple.com/thread/5523984?answerId=24506097022#24506097022