Cannot move songs from 'Purchased' playlist on my iPod (touch 8gb)

Soooooo I've purchased a handful of songs on my ipod touch and I cannot move them back to iTunes or to another playlist.
They are all listed in the Purchased playlist from the device.
Only one shows in the Purchased on [device] under Store in iTunes.
Also, they show up under the playlist in iTunes I moved them to but not on my iPod.
I've updated my iTunes software and my iPod, as well, without progress.
I'm not sure if I'm missing something or if there is a larger issue at hand.
Thanks for reading

Are the chapters of the podcasts separated as individual files or are they a part of a single large file?

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