Error 50/53 and other related numbers

Hello, yesterday my ipod classic started having trouble playing songs. It would attempt to play some songs and struggle to do so. If it did manage to play the song, it would only manage a few seconds before skipping to the next song that it could easily play. I figured it just needed a little reset and did so but the ipod still had problems. Then I tried synching it with iTunes but no improvement. Then, I decided to restore it and start from scratch.

It started synching and after awhile, it would stop short and say X song couldn't be copied to the ipod because of an unknown error: -53 (50 and other numbers have also appeared). Now I've done some searching already and tried numerous things already but nothing helps the situation. The most recent thing I tried was suggested here http://support.apple.com/kb/TS1539 and that didn't work. I then tried restoring the ipod and checking for hard drive errors, which it would detect and promptly fix but the ipod still failed to synch.

However, after going through topics here and searching online, I have narrowed it down somewhat. While slowly synching songs by the smaller playlists (as my library has about 7000 songs), the ipod seemed to have no trouble as songs were copied quickly and without issue. But once I broke 1000 songs, it started struggling again. There were no error messages yet but I do believe the problem lies with the amount of data it's trying to copy. The only problem is, I have a 160 GB Ipod Classic so there shouldn't be any issue regarding available space. Even in iTunes, it says I have over 118 GB of data available if I were to copy the entire library. I recently found this topic https://discussions.apple.com/thread/4171036?tstart=0 but it seems to apply to Windows 7 instead of Windows 8 so I don't know for sure if a disk quota is the issue. Also, I have no idea on how to check the disk quota on Windows 8 (if I can check it at all).

I really don't want to shell out $250 for a new ipod unless all options are exhausted. I'd take it to the Apple Store but my Applecare+ warranty already expired and if I recall, I can't purchase a new one. Can anyone help me? Please?