Need expert help - iPod Classics will not play recently downloaded songs

Sparknotes version of this question, so you don't need waste your time if you aren't interested:
-iPod Classic skipping over songs
-problem with iTunes transferring the files
-need help ASAP, we DJ with these iPods most weekends
Multiple iPod Classics are skipping over songs and will not play them.  This is a recent issue and these ipods are not new - we have been using them for several years now.  The playlist and the Macbook from which the playlist came are also not new.  The playlist copies onto the ipod so that i can see it on the device, but after unplugging the ipod and trying to play a song the screen just gets stuck for a few seconds, with the play symbol showing in the toolbar, but then skips to another song until it can find a song it can play. 
After some investigating i found that my itunes must not be properly copying the playlist - it shows up on the ipod, but when i view the ipod contents in itunes, that playlist is not there.  Upon a second attempt at copying the playlist to one ipod, i found that all files still show up in the song list, some files are now playable, but not all.  My husband and I are DJs and one can understand that this is quite a predicament, when all of our ipods suddenly only play certain songs.
Restarting the ipod does not solve issue.  Again this is an issue with multiple iPods, so i am thinking that maybe it is an iTunes problem but i don't know where to begin trying to fix it.  One thing i did notice was that when i plugged the ipods, iTunes sat in the "verifying iPod" stage for quite a while.  I found some past forums that touched on this but it seems to usually be connected to updating the version of iTunes, and i have the most current version (10.6.3).  This playlist was made years ago and the files should not be corrupt, at least they have worked fine in the past.

I find this concept worth considering. http://en.wikipedia.org/wiki/Bathtub_curve
The one year limited warranty ought to see you through "early failures". I have a sneaky suspicion that extended warranties are intented to cover "random failures" before "wear out" failure becomes likely which is why such cover is often limited to 3 years, the period when it is least likely to be needed.
In your case, assuming there is no obvious physical cause that has been overlooked, it would seem to be a random failure in years 2/3. Not common, but they will happen to someone.
tt2

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