There are more-convenient ways of getting your iTunes playlists onto your BlackBerry than physically plugging in your USB cable and transferring songs in a block. For example, you could use a program like Music WithMe, which is actually a dual-part system composed of a desktop component that scans your iTunes library for playlists, and a BlackBerry app from which you can pick the songs to play.
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 during testing. What it did transfer over played on the BlackBerry's built-in music player as expected.
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.