Thought I would share with everyone because alot of you like me were frustrated with the limited options on 360 to get songs on the HDD.
Someone at xboxscene.com has made an amazing program called XBOX Music Organizer which allows you to place songs on HDD without ripping. IMPORTANT: music files must be in .wma format
Check it out!
http://forums.xbox-scene.com/index.php?showtopic=717422