About a month ago, most of the Album art on my iPod just up and disappeared.

So, about a month ago, for no apparent reason at all, almost all of the album art on all of the music on my iPod just disappeared and was replaced by the default white art. It even happened to most of my purchased music! As time passed, some of it gradually re-appeared, which is really weird, but most of it is still gone. I have 174 albums on my ipod and about only 1/4 of them have art. Before this problem happened, almost every single album had art. I meticulously spend HOURS adding really nice album art to the music on my iPod, and then this happens.
I'm genuinely quite upset. I use my iPod a LOT and have put a lot of money into Apple. A problem like this should not be happening. I'm actually very tech-savvy (going to be getting a CS degree) but this problem baffles me at every turn and it's extremely frustrating.
So, last night, I tried to fix the problem again. I made an album in my music folder and added the proper information to each song, with an album cover (500X500 - all of my album art is 500X500) in the folder where the songs reside. I then plug my iPod in and open iTunes. I then go into file and add the album to my iTunes library, and then I go to the songs and add the album cover to their information via the "add artwork" submenu of the get info on the songs. I then sync the songs to my iPod normally, and the album art shows up on them. Great. Wonderful.
I then think, "Oh, maybe I can fix all of my OTHER album art manually!".
So I go to my artists on my iPod and find an album titled Asteroid (it's a song by Rameses B) which doesn't have a cover but should. I deleted it off of my iPod. I then plugged my iPod back into my computer and tried to re-sync the song Asteroid back onto my iPod but nothing happened. It WOULD NOT, and I mean WOULD NOT sync that **** song to my iPod. It just sat there like I never did anything at all. My method of syncing is that I find the song and drag-drop it to the iPod menu on the right side of my screen.
So then I kind of gave up for the night. It was midnight and I was done with this **** after trying to get that song to sync for at least 20 minutes.
So I eject the iPod from my computer (SAFELY) and close iTunes normally, bla bla bla, go to sleep.
I get up this morning and go to my music app and ALL OF MY ALBUM ART ON EVERYTHING IS GONE. *POOF*, gone. Including the songs that I'd synced last night! What the ****! How does that even happen?!
Some more information:
I'm running Windows 7 with a fully updated iTunes. My iPod is fully updated as well. As in iOS 7.1.0, non-Beta. It's an iPod touch 5th generation.
So, my question is, how the heck do I get my album art back on my darn iPod?! I have tried manually re-syncing individual songs after deleting them off of my iPod and they won't re-sync. I have also tried re-syncing my entire music library to my iPod, and the result was the same as before. Most of the album art didn't transfer to the iPod.
I'm extremely frustrated at this point. I'm at the very verge of jailbreaking this thing and iFunbox-ing all of my album art over to it forcefully. If Apple can't fix my problem, I will. I'm at that point right now.
Please help.
Thank you so much in advance.

Have you:
- Restore from backup. See:                                                
iOS: Back up and restore your iOS device with iCloud or iTunes
  - Restore to factory settings/new iOS device.            
If a PC
Removing and Reinstalling iTunes, QuickTime, and other software components for Windows XP
or              
Removing and reinstalling iTunes and other software components for Windows Vista, Windows 7, or Windows 8

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