The new update doesn't allow me to add songs to my iPod

I recently updated iTunes on my Windows computer. I got songs (not from the iTunes Store) and attempted to put them on my iPod. I had made a playlist with songs in it which is on my iPod, but it doesn't come up as an option to add the songs to it. I create another playlist with the new song's but it won't go onto my iPod. I tried everything, clicking and dragging, restarting iTunes, unplugging and plugging in my iPod again, syncing multiple times. I was going to sync through the Setting part of iTunes under my iPod, but it doesn't recognize my iPod from the previous version of iTunes. The songs work on iTunes, but they just won't transfer to my iPod. Thanks for anyone who can help me out!

Generally if syncing doesn't work as expected take the following steps:
Backup device.
Restore as a new device.
Restore the backup made earlier.
This assumes all content on the device is in your library already. If that isn't the case see Recover your iTunes library from your iPod or iOS device.
tt2

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