How do I add songs from my purchase list to my ipod nano?

I am at my wits end! I have an Itunes account. I have songs I've purchased. I'd like to add and remove some that are currently on my Ipod Nano, but I can not seem to get that to work. It used to be simple, where'd I'd just drag the songs over to my Ipod that I wish to add. Now, that option does not seem to be available.I am working on a Windows 7 Toshiba laptop.
On the screen when I log onto ITunes, on the left is a list starting with purchased, Genius, playlist etc. When I plug my Ipod Nano up to the computer, it does pop up in the upper right hand corner, recognizing it's there, but that's all. If I click on it, it disappears. It I drag songs from play list to it, nothing happens. It's so frustrating. I have been stuck listeing to the same playlist for months now. I thought by creating a new playlist, while my Ipod was plugged in, it would sync the songs to it, but that didn't happen either.
I read that I need to go to Devices, but when I finally found that, that was of no help either. It almost seems as though it's not recognizing the Ipod.
Please help!

To what iTunes library is the nano normally synced? The iTunes library you use (i.e. all tracks are in a single iTunes library). An iTunes library in a different user account on that same computer? Another computer? We need to know your setup and scenario before we can offer intelligent advice.
Regards.

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How do I add songs from my purchase list to my ipod nano?

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