Can't copy MP3s to iPod

I appreciate this has been asked before, but none of the search results turned up an answer I hadn't tried and failed.
I can import MP3s into iTunes, but I can now no longer transfer the files to my iPod.
For example, I use File->Import to import a .m3u, it successfully adds that playlist to my library, and I can play the tunes through iTunes. However, if I then try and drag that playlist from my library onto my iPod in the devices list, it creates a playlist on the iPod, but fails to copy any files. It doesn't throw up any error message, it just leaves an empty playlist there.
This definitely worked until two days ago.
For the record I have tried:
* Latest version of iTunes and iPod software
* Two different cables.
* Three different PCs.
* Resetting the iPod.
* Restoring the iPod.
* Resetting the warnings (but it still will not tell me why its not copying)
There appears to be nothing wrong with the actual drive in the iPod. It's clicking a little, but it always has done. And I copied 29 1GB files to it to check the integrity, and they were fine.
For the record, I just use the iPod as an MP3 player, I don't have any iTunes format files to test with.
Can anybody help me?
Message was edited by: subi211

I thought I had - until I tried dragging them to the Library->Music section, rather than onto the playlist I had created in the Playlists section. It's weird, but if I do the latter, then it goes through the whole "Determining gapless playback" thing, but once I quit out of iTunes, it can't find the files when I load it up again!
But dragging them onto the Playlist section doesn't throw up an error, and I get the + symbol on the pointer. So I thought it was importing correctly.
Okay, it seems I can't import playlists anymore, I have to drag the individual files into the library, then manually insert them one=by-one into the playlist, otherwise it loses them. Ah well, stick that one on your list, will you Apple?
Thanks for the help!

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