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Hard Drives and memory can degrade over time so, the area where some songs are located on the drive/memory the physical media itself may become slightly damaged or corrupted.  If it's really 1/5 songs where it's happening, you may want to reformat/reset to factory settings and reload all the songs through iTunes and see if that changes anything.

 

It's also possible (and more likely) that iTunes being what it is, may have damaged the files in a sync process, so again, I'd reformat the iPod and start over to see if that fixes it.

 

How old of an iPod is it?

You might also check in your iTunes, that the song itself will play to the end.  I recall iTunes used to have a system that would allow you to go to the next song, and it would take off the last 3 (or however many) seconds from the song you were playing, to go to the next one. 

Check out the info in the song itself, command i (mac) or right click win on the song, there used to be info in there that allowed you to cut off a song at a certain time period.  Make sure that the times are set to the max values. 
Like CaPackFan said, bitrot isn't very likely.  Its probably in your preferences somewhere.  Or, if it were from a CD, the SW used to import it may have cut it off, I think there were a few versions of the itunes on mac a long time ago that had a few problems like that.

the songs on Itunes seem fine, and it is a lot more than the last 3 seconds that are lost.

 

Ran it again yesterday, I exaggerated with every 5th song, more like every once in awhile.  

 

Gonna try cleaning the whole thing out and starting from scratch.  Needed to add more Lorde to the playlist anyway.  

 

 

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