Imported songs and some songs bought through itunes aren't playing on my ipod?

Hey I just updated both my ipod and Itunes, and while syncing new music to my ipod touch (5th gen,) it seems half my music had gone haywire. Some of it is stuff I've bought from bandcamp, downloaded from Itunes, or uploaded from CDs. They all worked fine till I tried syncing new music. Any idea on what's going on? Is it the update? I don't think I did anything that would prevent these files from working. All imported music files are AAC or mp3 and have worked in the past.
As an added note, while looking at the music files through itunes as the ipod was supposed to be downloading them, they usually get a little loading circle, but the entire song was greyed out even though they were selected to load.
Also while trying to play pre-existing music in my ipod, it will skip and jump through songs till it lands on one that works. All the songs it skipped through will have an icon saying they are playing next to them when they are obviously not. Corrupted files? They play just fine on my computer though.

Try:
- Reset the iOS device. Nothing will be lost
Reset iOS device: Hold down the On/Off button and the Home button at the same time for at
least ten seconds, until the Apple logo appears.
- Unsync or delete all music and resync
To delete all music go to Settings>General>Usage>Storage>Music>Tap edit in upper right and then tap the minus sign by All Music
- Reset all settings      
Go to Settings > General > Reset and tap Reset All Settings.
All your preferences and settings are reset. Information (such as contacts and calendars) and media (such as songs and videos) aren’t affected.
- Restore from backup. See:                                 
iOS: How to back up                                                                
- Restore to factory settings/new iOS device.             
If necessary
You can redownload most iTunes purchases by:
Downloading past purchases from the App Store, iBookstore, and iTunes Store    

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