Problems copying music to ipod

hi, long term lurker joined up!
can shed light on this, driving me insane
ive googled , found many other people same problem no 1 ever posts solutions.

basically, have large collection of mp3's play correctly , have no issues @ all. none corrupt.

can put them itunes , play them, when try put them onto ipod keeps failing following errors.





if click ok can start syncing again, copy random number of files , fail again.
different files every time. have tried remove files fails on , makes no difference.
have reset ipod factory settings.
makes no difference try, keep getting same errors!
have tried sync load of them onto iphone , ipad same results.
copy 1 file , fail , if you're lucky might 10 @ once.
can files onto ipod, on 5000 songs takes hours of sitting there restarting

help!!!!

edit:
in example above, failed on song "touch", info file.
not corrupt , plays fine

 

for interested, think may on something.
ive died of boredom , synced majority of files, being more obvious same files failing each time.
however, because there quite few, did seem random @ first.
coupled fact open , play other devices , programs makes more confusing.

however, have picked out 6 kept failing , have re-encoded them in mp3 format (even though mp3's!) , after doing sync straight away!
difference between files after encoding smaller in size though encoded @ same bitrate.
strange, @ least have solution.
ive got re-encode 500 songs 1 one

 

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