I am having the same exact issue.
Have reached out to all my Pio contacts to see if I can get an answer. Will report back here and please do the same!
Hundreds of playlists and I would rather not risk re-installing if I can avoid it.
Like your case, everything in iTunes is fine, (10.7) but none of the new playlists or folders are being bridged into RB, even after hitting "refresh". (December 5th was the last successful bridge session)
Curious if the problem is easily fixed by upgrading to the new 2.0.2 software? Although I am avoiding that so far because other DJs I know who did the update said you are unable to drag and drop to device, amongst other bugs..
Would really like to get this back up and running in 2.0.1 without having to re-install :(
Hoping for a solutiion soon!