Well, I just had to sit and watch the consolidate process & I finally noticed that it was having problems consolidating one batch of files that were added to the compilations folder all in the same day, and the problem files had an accented character in the name (La Bohème).
So I moved them out of the compilations folder, and things went better. I reported it as a bug to Apple using iTunes > Help > Feedback.
So - if you start noting which files have problems, maybe you will notice a pattern or some similarities between the files that sometimes do not copy, such as if they are in the compilations folder, have special artwork, are they MP3, AAC, WAV, or whatnot...
Are you using auto or manual sync, by the way?
If using auto sync, perhaps it is a certain playlist causing problems? I'm not fmailiar with your library, obviously, so it's kinda up to you to figure out the pattern from here on out, but I think my advice is solid.
The album artwork folders store artwork that has been downloaded from the itunes store.
Message was edited by: Katrina S.