Trust me - OP's case is not the worst. At the least, OP can downgrade back to iTunes 10 as iTunes 10 still support the latest iPod Classic firmware.

My case is basically the "armageddon".

I used a factory unlocked iPhone 4S 64 GB from AT&T as iPod (from eBay). The phone feature is only used when I travel internationally. I used Google Nexus 5 in the U.S.

I have been resisting from iTunes 11 due to the elimination of the multiple-window feature. Since only iTunes 11 supports iOS 7, so I was kind of forced to upgrade the whole deal.

This is where my worst nightmare starts. I manual sync my content. I have been experienced multiple issues with syncing. In the end, synced content has been disappeared (mostly songs). Since I have to manage my own playlists (this is why I hate iTunes 11 without actually using it), so imagine how this is a PITA situation for me. Since my upgrade to iTunes 11 and iPhone 4S (from iPhone 4) from last September, I have restored the iPhone more than 10-20 times, including DFU restore.

The best part - every time, I almost had to restore on each iOS or iTunes upgrade.

Some of you may criticize maybe I bought a defective iPhone from eBay. I can assure you that's not the case.

And of course - I did experience the famous DVD issue as well.