I got Motorola Media Link to do the job for me. I wanted to move my music which was indexed by iTunes and keep the playlists. Media Link needs to have a bit of setup choices made, but it does work - at least for my good sized library. Here are some helpful comments I used and copied from another forum.
Motorola Media link makes it easy but you have to make the correct settings. Motorola does not make this easy with their horrible instructions. After you download the software go to settings (top tabs), click music (on the left side tabs) then click itunes. Go back to Music on the top menu and click it all your itunes playlists should show. Select a playlist then go ahead mount your Droid (you have to look at the notifier bar on the top of your droid and a USB symbol should show), press on it and mount it. After the Droid is mounted your can sync it, a window will come up and be sure to look at it carefully because there is either a preference tab or music tab and you need to set the correct settings. (Sorry can't pull it up without the Droid mounted) For some stupid reason they have default set to copy music from your droid to your computer and I wound up with voice commands for directions in the music on my computer...... ugh stupid settings. Check your preferences it so it copies to the droid, the motorola screen shots are terrible, very blurry, but take a minute to look at those tabs on the Sync window because if you reset them it works perfectly. If the settings are right it will show the number of songs it is transfering if it sits there and just churns the settings are wrong. All album names, artwork and track and artist names transfer perfectly from itunes. Media link doesn't work with monster lists or libraries like 2 thousand songs but a few hundred at a time works really well. Hope that helps, I have several Itunes playlists and everything transfered beautifully, artist album, song and artwork, but it didn't happen the first time until I reset the sync preferences
