You can if you are synced to a PC. All the music files are stored in the my music/itunes/music folder. I just switched to a droid from an ipad. All I had to do was drag and drop. No adding songs, then creating playlists, then syncing. Much easier. I am not an Apple hater (2 ipads, 3 iphones) but I hate Itunes. Biggest pain in the ass program I have ever used.
The thing I don't like about this legal concept is that is sounds like the government sending a representative to look over Hank Reardon's shoulder in Atlas Shrugged.