You can do it from iTunes without any hassle at all!!
1.Make sure that everything that you want is on your iPod and delete everything from your library. (This is just to clean it up or back up the iPod)
2.Click on File and then on Add folder to Library. Wait until it copies all of the names of the songs to your library.
3.Click on advaced and then on Consolidate Library. This will then copy all of your music into your music folder onto your hard drive.
That's it! I have did this many many times even though when you ask Apple, they say that it is impossible.
