There are easier ways of getting your iTunes playlists onto your BlackBerry than plugging in your USB cable and transferring songs in a block.
As did Simplify Music (an iPhone app,) Music WithMe's dual-part system has a desktop component for Windows computers that scans your iTunes library, as well a BlackBerry app from which you can pick the songs to play.
Unfortunately, Music WithMe didn't pan out as promised during our tests on a BlackBerry Bold 9700 and a Windows XP computer. Syncing took some time, as is to be expected, but the app could do with more helpful hints communicating the estimated time remaining in a sync and more importantly, when you've stopped syncing and can start listening.
The more major complaint is that the app only recognized some, but not all of our playlists, even after running through some of the protocol that the company suggested when we presented our findings. Music played on the built-in music player as expected, however.
The technical difficulties keep us from recommending the app without caveats, though Music WithMe might work on your computer and BlackBerry without a hitch. We find the $14.99 one-time purchase price a little steep for something you can essentially do yourself for free, but audiophiles who frequently change up their iTunes playlists may appreciate the convenience of remote automatic updates on their BlackBerry. Luckily, the free 30-day trial gives you plenty of time to decide.
Music WithMe is compatible with BlackBerry phones running OS 4.5 and higher, iTunes version 7.1 and up, and Windows XP, Vista, or 7.