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this programme definetly works-> senuti (itunes spelled backawrds :D) its free ( well you can like transfer 250 songs before it asks you to pay) not only does move music from the ipod but photos and videos !!


update : lol i didn't read your whole post xP the only way i know is to transfer songs etc.
is with a proggrame :S
 
If you have songs on your iTouch that aren't on your Macbook's iTunes library, when you plug it in to sync a message should come up saying that it detected songs on your iTouch that aren't on your Macbook, and iTunes will ask if you want to move them to your Macbook. I believe it's not just for purchased songs, you can move songs that are AAC, MP3, etc. as well.
 
If you have songs on your iTouch that aren't on your Macbook's iTunes library, when you plug it in to sync a message should come up saying that it detected songs on your iTouch that aren't on your Macbook, and iTunes will ask if you want to move them to your Macbook. I believe it's not just for purchased songs, you can move songs that are AAC, MP3, etc. as well.

iTunes will only do purchased music. If you have other stuff you put on, it will delete it.
 
Senuti is the way to do this and it is one of the single greatest iTunes apps available. That would be the way that I would transfer songs off of my iPod Touch.
 
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