Music in iTunes - but will not manually sync when I drag to iPod

Hi There -
I have ripped a bunch of stuff to my iTunes, and checked - all the music plays just fine.
I manually manage my iPod - so I created specific playlists, dragged the items from iTunes to my iPod.
It shows the items in the playlist, but does not give me an idication that they are being moved.
When I try to play in my iPod they won't play. When connected to the computer, I get an '!' next to the song. When not connected to the computer, it just runs through the playlist within a second and goes back to main menu.
Any ideas on how to solve?
Thanks in advance for the help....

I am replying to this as it is still unanswered - - is there anyone out there that has encountered this and has a solution?
Items ripped to iTunes and play just fine
Create a playlist in my iPod
Click and drag songs from iTunes to iPod
Shows items in the list, but does not show them being transferred

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