I finally found a way to automatically sync my Windows Media playlists to my Motorola Droid.
http://www.motorola.com/Consumers/US-EN/Consumer-Product-and-Services/Software/Motorola-Media-Link-US-ENPreviously you had to manually create the playlist on the Motorola Droid after you had copied/sync'd the actual music files to the Motorola Droid. Now Motorola has a piece of software called Motorola Media Link (apparently written by the folks from Nero) that will sync not along your Music, Pictures, Video and Podcasts but will also sync your playlists.
Awesome!