Ok, instead of transferring your entire ITunes library on your Droid, what about transferring your favorite playlists; its much easier and you only get the music you want right?
Even before I had my Droid I've been using a little program called "ITunes Export UI" and it is the fastest and best way to export all or individual ITunes playlists with or without the actually music files.
I would suggest choosing with the music files and it will export the Playlist and Files and place them in a folder together, than just take that folder and put it in your music folder on your Droid; the next time you open your Media player click Playlist and you will see your newly imported Playlist.
You can download it
here