IPod classic fails to sync some tracks from iTunes

I use an iPod Classic 160 GB with iTunes. Both are fully up to date. Every time I sync with iTunes roughly 500 of 5000 odd tracks fail to sync. This number fluctuates, but stays around the 500 mark. iTunes does not recognise this problem - it claims to have synced completely. It is only when I go through certain Albums I notice that some tracks are missing. It tends to affect the same artists, but different songs are missing within any given Album each time. (ie: a song may appear on the iPod one try, then be gone the next.)
All my tracks are either AAC audio file or MPEG audio file. The problem seems to affect them irrespective of kind.
There is plenty of space on the iPod, with over 100 GB free.
I have tried Retry, Reset, Restart, Reinstall, Restore - all multiple times, with no result. I have tried syncing auto and manually, and wiping both iTunes and iPod every way I can think of. Still, when I sync, the problem remains.
This problem is driving me crazy, especially since I can find no cause, and no applicable advice on forums. I have searched Help forums for answers, but everything that comes up either doesn't match or I have already tried with no result.
Please help.
If I need to give more detail for an accurate diagnosis please let me know.
I will be eternally greatful to anyone who can help.
Thank you, Jonny.

I'm also having the same issue. I have recently had to get rid of my old PC that my ipod was synced to and so have now had to sync my ipod to my new laptop. The problem started as soon as I did this - at first it was saying that my laptop wasn't authorised in the itunes store, but it is and I have reconfirmed this. All of my music was copied across from old computer but there are around 2000 songs not syncing. If anyone can help it would be hugely appreciated, it's driving me mad! One other thing is that I went to download all of my previous itunes purchases to this laptop but only 3 of them actually downloaded - I had separately copied them across from my old computer anyway but wanted to keep the list of my purchases - when I go into my account it thinks I have downloaded everything so won't let me do it again. I'm assuming both problems relate in some way to the new machine, but I don't know why.

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chicx wrote:
This is the third time of writing this on your Apple Support Communities!
Not with your current user id.
Far too much uneccesary information in your post, which only confuses things, a vast amount!
Let's start with iTunes.
Have you updated iTunes to 11.1.5, because the previous version did appear to have an issue about seeing iPods?
With iTunes 11.1.5 installed, look in Edit/Preferences/Devices, (or use the ALT key, followed by the E key and then the F key) and make sure that the box named Prevent iPods, iPhones and iPads from syncing automatically does not have a tick in the box.
Once you have doen those two things, check to see if the iPod is seen by iTunes.
chicx wrote:
By the way, what does IOS mean? (I thought IO stood for operating system, but am flummoxed by the S on the end.
Really?
OS stands for Operating System. (In computer speak, IO means Input/Output.)
iOS originally stood for iPhone Operating System, but it now refers to the iPod Touch and iPhone. The iPod Classic, which you have listed in your profile as your iPod, does not use iOS.
I assume that you have been listening to the Podcast in your iTunes on the computer as you cannot transfer it to your iPod. It's what I'd do.

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Adding new music, 'XXXX's iPod cannot be written or read'' can you let me know the number. most likely music format is not iPod Compatible like HE-AAC.
started skipping songs - these are normally due to corrupted ID3 tags, try converting them -File-> Advance -> IPOD version or use MP3 validator to fix all songs in the library. (My Apologies, only work for MP3 music that skipped)
As for item 2, you can try Hard Reset if you like to download MP3 validator.
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Select your preferred language.
Here is the Apple support Article on the 5Rs
http://www.apple.com/support/ipod/five_rs/classic/
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IPod classic fails to sync some tracks from iTunes

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