IPod Classic 160g Won't Hold Songs past 2 gigs or so.

Over the past few months my ipod classic had been having periodic playback problems. I listen to it at work and I'd say it gets a solid 6 hours a day on weekdays. It's about 3 years old. The issue was that it would pause songs every hour or so, then skip ahead four or five tracks and start playing normally. If it was a podcast, it would simply stop playing the podcast and not save my position. I put off updating it for awhile because it had a lot of music and I didn't want to have to reload it from my collection. But with this last update, I bit the bullet and did a full restore.
Now, the podcast no longer has playback issues, but it also won't allow me to load more than 2 gigs worth of music/podcast to it. Once it gets to a certain point, it stops loading music and says that files weren't copied due to an unknown error(the songs that it pauses on are random and never the same). Once it gets to this point, I can still browse my library while in itunes. However, if I eject the ipod, it tells me that there is no music loaded, even though the disc space is in use. If I reconnect to itunes, it tells me the ipod needs to be restored.
I've done this about 5 times now. I've also tried uninstalling and reinstalling itunes. Nothing seems to work. All of my music was legally purchased, and are in fact merely ripped from my physical collection.
I'm not sure if this is an itunes problem, or a problem with my ipod. I haven't seen this problem mentioned anywhere else, but I'm not quite sure what to do about it.
Also, if it weren't clear, I'm not very technically inclined.

It seems to be the hard drive. go and run the diagnostics https://discussions.apple.com/thread/3784647?tstart=0.

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My iPod recently began having issues, such as not playing songs that should've worked, skipping over them, etc. So I chose to restore it, and now it stops syncing songs at around 3 GB worth of music, and I'll either get error 1303, 53, or 69. I sync manually, no photos or anything besides music. When it gets to around 3GB full, the sync will start going really slow, and I can hear a weird crackling sound coming from my iPod, as if it's trying too hard, and then the error message pops up after this goes on for a while.
Here's what I've tried so far:
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- Disk Mode
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My music won't play on my ipod classic 160GB and it skips songs can anyone help me?

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IPod Classic 160gb won't sync a song?

My ipod classic 160gb wont sync a song, it just says this song wont play on this ipod. Is there anyway I can fix it? Or make it sync? Or something?

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What format is this song in? Have you tried converting it to another format via iTunes and then syncing the new version over to your iPod? See this article for more information on converting your track to a different audio file format in iTunes.
http://support.apple.com/kb/ht1550
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After I installed the latest itunes on my new PC, I used it to restore my ipod and syncing music.
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normally if connected to the low power USB 1.0 port at the front of the PC.
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Antivirus or other plugins conflict with iTunes - Stop the Antivirus and plugins,
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My Ipod Classic (160G) no longer synchs completely with iTunes (93G). Have reset and restored to no avail. AM about to try roll back to a previous version of iTunes, which has been on auto update.

My iPod Classic (160G) used to sync flawlessly with iTunes (93G).
Recently, there seem to be fewer folders syncing. In particular, it is not syncing more recent adds. It also occassionally refuses to sync at least one mp3 downloaded from Amazon.com, giving an unable to sync message with an error code or 50.
I'm running iTunes version 10.7, and the software (2.04) on myiPod is current.
I only use the iPod for music. I have only one playlist.
Reset and restore did not fix the problem; I'm considering rolling back to a previous version of iTunes. Are there any other ideas to consider?
Please advise.
Thanks,
R

giving an unable to sync message with an error code or 50
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https://discussions.apple.com/thread/3924425?tstart=0
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The songs from the Sony MP3 player need to be imported into your iTunes library first before they can be synced or added to your iPod Classic.
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If you are having issues with your iPod Classic not responding, you may want to try the steps listed in the following Troubleshooting Assistant:
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Ipod classic 160gb won't sync past the 36 gigabyte point

I recently had the headphone jack on my iPod Classic replaced, but when I got it back and tried to sync it on my computer (running Windows XP SP3) I began to encounter serious problems. When the sync reaches the 36 gigabyte mark (I can't say for sure if it always crashes at exactly the same point), the ipod will refuse to add any more music and I encounter one of three error messages, one about being unable to write itunesdb.old, one claiming the ipod is full and one claiming it encountered a crc error (alas I can't remember the exact wording of any of the three, I can get this information with some effort if it is really necessary). Furthermore, after this error occurs, the ipod causes the computer to behave sluggishly, with the 'my computer' folder frequently freezing when I attempt to open it. Also, when I attempt to eject the ipod it goes into a reset (but for some reason it will still play all music added before the last sync attempt perfectly).
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Ipod classic 80GB won't sync.

Hi, I posted in another thread and was advised to start my own discussion.
I have an ipod classic 80 GB from 2008 that runs fine except that in the past few weeks it will not sync with itunes 10.4.1 on an old MacBook white from 2006. I had not synced in a while but when I wanted to update a playlist it freezes itunes completely, usually right after it prompts me on whether or not I want to restore purchases no longer present in itunes. In some other topics I've seen suggestions to wait it out to see if it will sync eventually while the beach ball spins, but after 20-30 minutes it still won't sync.
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IPod Classic 160g Won't Hold Songs past 2 gigs or so.

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