Authorization error message in iTunes when transferring music to iPod

This has been driving me nuts. I have a 30GB iPod w/ the color display and a brand new Intel MacBook with the latest version of iTunes (iPod's been updated as well). My previous computer, a Powerbook G4, fell off a counter and died on the spot, so my only back up for all the music I have is what's on my iPod.
First, I couldn't transfer all of my music from my iPod to the MacBook because of an authorization problem with iTunes. So, I authorized my computer, which still didn't solve the problem. I resorted to using iPodRip which successfully got all the music off the iPod and onto the MacBook. No harm, no foul.
The problem now is that I can't transfer music from the MacBook to the iPod for the exact same reason: I get the error message saying that some songs are not authorized to play.
I have tried the following things:
1) Deauthorizing and re-authorizing my computer on iTunes = No luck. iTunes informs me that I am now authorized and that I have 1 out of 5 authorizations in use, but the songs still won't transfer.
2) Playing an "unauthorized" song in iTunes. Again, I get a message asking me to enter my account info and then thanking me for authorizing. However, the song won't play in iTunes, nor will it transfer to the iPod.
3) Restoring my iPod to the factory settings. Not sure why I tried this, but it didn't work and is the reason why I no longer have all my songs on my iPod and am trying so desperately to get them back.
4) Used iPodRip to try to reverse the process, but again, no dice.
I have a feeling that the answer to this is stupidly simple and I'm somehow missing some crucial step somewhere. Can someone help me out?
Intel MacBook Mac OS X (10.4.7)

Alright, I think I solved the problem on my own. For what it is worth, restarting the computer seemed to solve all of my issues. After restarting, iTunes accepted my authorization (alerting me that I now have 2 of 5 machines authorized) but my iPod kept disconnecting after syncing. So, I reset the iPod, downloaded iTunes 7 and reinstalled it, and whaddya know- It works! I have all of my music on both my computer and the iPod.
It was stupidly simple, too.

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Authorization error message in iTunes when transferring music to iPod

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