"Some of the items in the iTunes Library...."  "Could not be found"

I have 53 tracks out of about 1500 that can't sync. I can play them just fine in iTunes, but they won't transfer to my iPod Touch (gen4). For example, I have a play-list of a particular album and half of the songs transfer and the other half don't. iTunes will play all the files however. The files are located on a network drive (NAS). I can play these files also via XBMC or WD TV Live.
Thoughts on how to resolve?

Thanks Katrina for all your help.
I talked to an Apple tech support person. Actually, my call had to be elevated to the next support level. Joy. You are correct, there are multiple listings of the files in the error report even though there is only one copy.
The support person had me do a few things. Here is what eventually seems to fix things:
1) For the mp3's that DID copy but were listed as not found... Some files were duplicated so deleting the duplicate with the "!" was an easy fix. I found one file that I could search by song name in iTunes but could not find it by song name search on the iPod. Looking at the iPod playlist I found the file listed by the filename (not song name) and the file played fine. Then in iTunes I double clicked on the song name ("!" showing) and selected locate. I then pointed to the location on the NAS. Resync and now the name of the song on the iPod changed from filename to song name. The file was no longer listed in the error report.
2) For the m4a files that didn't sync... the problem songs appeared three times in a search in iTunes. Two of the listings showed the "!" next to the name. I deleted these two for each song that didn't sync and all transferred fine afterward.
Perhaps there is an issue with ID3 tags since I use filenames more than tags in organization. Still, I would think that iTunes would not get so confused or be a little more friendly with its errors, especially considering how long its been around.
Thanks again for your help. Looks like I have a manual way to correct this issue.

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