For what it's worth I use the BB plugin for iTunes, I think it's Media Manager (NOT the thing that is used with DM, this one is standalone and does not have anything to do with Device Mgr). Open it, plugin BB, and transfer playlists to BB. The downside is you can only move things that are playlists, so I make temp. playlists of albums/artists that I want to move. The upside is all the artwork is there and the genres/artists/albums/songs organization is just like iTunes. And it's fast. The drag/drop to card method worked but not all of the album art would transfer over. I have the original .114 OS so that's not been a problem for me (yet).
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BB 8900 Tmobile, Moto Droid Verizon
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