RIM has been busy, and besides the Windows Live Messenger it has launched the Media Sync application which is now available for some BlackBerries: the Pearl, the 8300 Curve and the 8800.
With the Media Sync application will allow you to sync music playlists from Apple's iTunes and update playlists with iTunes. We are talking about non-DRM files only here. With Media Sync you will constantly have an updated BlackBerry as far as music is concerned. You will even have the option of controlling the amount of music you can access according to your microSD card size. The application comes free from RIM so try it whenever you feel like it.
Media Sync for BlackBerry
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