Large playlist some songs aren't lodaing onto iPod

I have a very large playlist and there are four songs in it that are perpetually not loading onto my iPod.
I've checked file types and all my tracks are in mp3 format, I've even reformatted the bitrate of every song I've got just in case.
But the problem remains, I have no idea how to find out which four songs aren't loading properly.
I've checked my iPod and Mac playlist and they both have the same amount of artists and albums.
Any ideas would be appreciated.
-Bobo

What format are these tracks in and what is the original source? Are these downloads from the iTunes Store or were they imported from outside of iTunes?
Have you seen this article yet?
Troubleshooting songs that skip
B-rock

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