Transferring purchases from iPod to new computer / Authorization

Question

I recently purchased a new Dell laptop and downloaded and installed iTunes. I've authorized the laptop, so now i've used 3 out of my 5 authorizations (old PC, work computer, and new laptop). I bought 2 albums off of iTunes at work and was able to transfer them to my new laptop with no problems. When I try to transfer the other 15 albums I bought on my old PC, however, it says my laptop is not authorized to play them. It's obviously authorized since I was able to transfer SOME of my purchased music, so why is it saying it's not authorized?? When I called Apple support the other day at 5:50, the guy put me on hold for five minutes and then just hung up so that when I tried to call back it was after 6:00 and they were closed! Nice customer service, Apple.

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.