Ipod Classic no longer plays certain songs.

My Ipod 160gb Classic has been working correctly as of lately (or rather, how it usually acts instead of correctly); however, yesterday I plugged my Ipod into my Windows XP computer, Itunes Version 10.1.1.4. After resyncing/connecting/etc. that the Ipod always does when it is plugged in and letting it charge, I eject my Ipod through Itunes.
Then, much to my delight, my Ipod was somehow managed to be wiped. No music, no videos, photos, podcasts, etc. However, I did find it interesting my game stats were still there, so I assume the Ipod just didn't decide to do a whole harddrive delete (I may be wrong). I tried the Center Button + Menu combination for the X amount of seconds, for the Apple Logo to appear. No dice, still nothing.
But anyway.

I now tried to plug my Ipod into my computer again, and kept receiving errors saying it could not be read due to an Input/Output issue in reading my Ipod. This could have been the USB port, but that doesn't change the problem I have currently having.
So once the Ipod was read (took forever and Itunes kept freezing), I restored it because Itunes told me there was an issue with it. And you know, I had nothing on there, so why not. After restoring, and resyncing all 750 of my songs from Itunes (took forever. All of these songs either bought through the Itunes store, or through a CD I own (I can supply photo proof of these to show the issue isn't from pirating)). But anyway, after resyncing all these songs, a huge issue occurs that I am unable to fix. Certain songs will only play for around 5 seconds, then not play the rest of the song, and continue to the next. Or won't even play the song at all.
Ex: Song 1 on an album will play, then the next song to play is Song 5, skipping 2,3,4 in between.

Sometimes certain songs will play, other times they will not for no reason whatsoever. It's frustrating when I try to play a song and it'll work, then I'll try listening to it a few hours, or even minutes without turning off my Ipod, and it won't play now. When I try to manually select a certain song that isn't playing, the Ipod will freeze for probably around 10 seconds, until it ends up skipping every song in between until the next 'playable' one comes up.

All of these songs work on Itunes currently, and worked before the issue I had with all my media being wiped from the Ipod.
I checked the file format of some of these songs, comparing not working to working, and they are the exact same. The issue is occuring with both songs from CD's as well as purchased from Itunes. Again, all of these songs were bought legally.

I searched through other people having these similar issues, however much of the way those were fixed aren't working here. I tried several of those solutions: restoring, converting files formats, making sure Itunes Store purchases, etc, and I'm pretty tech-savvy But the thing is, all of my songs worked before, now they don't, and I just can not figure out why.

I hope I supplied enough information on the issue and how it happened. Sorry for the huge message. Help is appreciated 🙂