Can I rescue my iPod? corruption problems

My iPod Classic has been working seamlessly for 6 years, but lately a series of problems developed.

A few weeks back, after connection/synching to my iTunes, it suddenly declared that there were no files any longer-for no apparent reason. (There was 90gb of files previously). I had to do a Factory reset and painstakingly reassemble all my files.

Since then it has worked well for a month, but then in mid-playlist it suddenly stopped, would not respond to pressing 'Play' or anything else. I connected it to iTunes, it took a long time beachballing to show up there, and it showed only 20 of the 40 or so tracks I had just played. There was (briefly) mention of corrupted files.

I have it set to 'Synch songs manually', and tried to add/remove a few tracks, thinking there might be a corrupted file among the ones I'd just played/was about to play. They appeared to be added/removed, but when I tried to eject the iPod, it said the iPod could not any longer write or delete anything. Also it would not eject properly and I had to just unplug the cable to get it out of iTunes.

This behaviour persists-(can't write anything, won't eject properly, beachballs continually in iTunes), but it still displays normally, tracks play etc.

Also I regularly back up the iPod Control files using CarbonCopyCloner, but last time I tried this CCC said there were 'infected files' and it would not complete the task.

-Is it toast?

-If there are corrupted files, how can I find them? and,

-if I buy a new iPod, will any corrupted files damage the new one too when I add all my music again?

-Could this be anything to do with Mavericks? (I'm on OS 10.9.2, iTunes 11.1.5)