ITunes will not transfer songs and podcasts to iPod

Whenever I try to synch, or manually transfer a song/podcast, I get an error message saying that the is "not enough room". But when I open the device through iTunes, it shows that there are only two songs on it. I tried restoring iTunes and I ran the iPod reset utility (it did nothing). when I look in the manual, it tells me to go to places (ie: the settings tab) which do not show up on my iTunes. How do I get this device to start accepting downloads again?

Try it again... It works! New iTunes version
I have had the same problems, for years it seems. Shuffle Gen2 (I have 2) would tie up iTunes for hours. Restore, utility, reset--nothing would let me update songs on the shuffle (except using a Mac). The swarmy Apple genius workers did not know the answer; they would only say that it works on Macs (which was true, it did work on my Mac notebook BUT my library is on a Windows desktop).
Anyway, I decided to try this again today. Success! Using iTunes I guess they fixed the bug.

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