Are your songs DRM protected?
Do you know what the size of your playlists actually are? Media Sync has a setting where it limits the amount of space it can use on the Media. I would try transferring small playlists first and work your way up.
8830 -> 8330 -> 9550 -> 9650
Just think about how far BlackBerries have come from then till now... And what else is coming.
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