Will "Transferring Purchases" from my friends ipod wipe the other tunes?

Question

I copied a load of tunes, purchased and copied from CD, etc to an I-pod nano and gave it to my friend as a present. I have since "lost" a lot of the tunes :0( when trying to transfer stuff to an external hard drive, nightmare..!! anyways, I am having no sucess re-copying the music back to my PC. The only option seems to be "Transfer Purchases" but I'm worried incase it wipes the rest of the songs from the i-pod. If anyone can help get my songs back I'd be most grateful. Music is Life...!!

Answer 1

There is authorization and "authorization"
I did a similar move. I replaced my Itunes server with a new build. I successfully saved off the old Itunes folder to my Network Attached Storage box and later copied that archive from the NAS into My Music on the new Itunes server.
The Itunes folder contained different types of data.
For CDs I loaded DIRECTLY into Itunes, the data includes authorization to play the data - because Itunes verified that it was an origional CD that was played directly into Itunes.
In a similar manner, if you have Itunes data that was purchased and downloaded from the Itunes Store, then you need to "Authorize" the computer with Itunes in order to play that Itunes Store procured data. This is the "you have done 3 of 5" authorization.
Finally, for CDs that I loaded into my old server via Windows Media Player, when I did a consolidate in Itunes, it went out and found the WMP data on a disk I dedicated to WMP music files, and since it was authorized in WMP, Itunes would play it. When I went to the new server, Itunes had the Itunes version of the songs in its library, but would NOT play the songs that had been migrated into Itunes from WMP until I actually connected the hard drive with the WMP files on it so Itunes could satisfy itself that it has "autorized" copies of the music. As soon as I connected the Windows Media Player data drive, Itunes did a compare and updated the Itunes versions of the songs imported from WMP to authrized and plays them just fine.
The alternative is to reload from the origional media.
Hope this helps.