Isn't the problem with media sync with itunes that itunes music from the itunes store is locked and won't work on your blackberrry?
That's right, anything bought from itunes that's not itunes plus (DRM free) will not play on the BB. If you try and sync a message will pop up to say it can't be played so wasn't transferred. If you have cd ripped music or DRM free trackes downloaded (Amazon, 7Digital etc) these will be fine and will sync across. Of course if you don't use itunes then none of this will matter in which case you'll just have to drag and drop as far as I know or I think there's Roxio also.