"not enough free space" msg appearing incorrectly. Unable to properly sync.

I have been searching through the posts and haven't seen one similar to this:
Initially, my nano worked wonderfully. Then, around Thanksgiving, anytime I tried to sync it with my laptop, I received an error stating it was too full to sync -- even if I wanted to have only one tiny file on the device. This week, I updated iTunes and used the iPod updater, hoping the problem would be solved with newer software. It didn't. I tried over and over with what came with the device and then what was online. I tool the device, my cable, and laptop to the local Apple store for assistance. After about an hour, I was told that the problem was my computer.
I went home and tried starting over from scratch using my desktop. I tried with the software that came with the device, with what was online, resetting, etc., etc. It still didn't work, so I went back to the store.
I was told it might be the cable as they were able to load songs from a Mac.
After whatever was done at the store, I have now managed to sort of get it to work once in awhile by manually updating files. But it only seems to sync one way --> from the computer to the device. I have to look at the device to figure out which podcasts I've listened to and now want deleted and then manually delete them from my computer instead of being able to look at my computer after a sync operation and seeing what was played.
It also now constantly displays a "Do Not Disconnect" message - even after being connected to my computer for hours. The online help is not helpful in diagnosing what this means. I did see some posts on this forum about the "Do Not Disconnect" message and am not as concerned about it as I had been earlier.
Why has it stopped working? It used to work just fine. I have tried using two different computers at this point. I don't think the problem is on my end.
Thank you in advance to anyone who may be able to assist me.

As of today, my device now skips songs and plays chunks of songs over and over.
I went back to the store again and have now been passed off to customer support.

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