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I would assume that if you do a clean install then yes, de-authorize it but if you're taking the upgrade path then you shouldn't have to. But you know what happens when we assume things...
 
Do I need to de-authorize iTunes before the upgrade?

Umm... I've never ever, never ever used this method. In the past I've upgraded from Mac OS9 → OSX 10.0 → 10.1 → 10.2 → 10.3 → 10.4 → 10.5 just via dragging and dropping the iTunes folder to the home directory of the system drive from my external backup, after update the software... I've never ever had any issues. Ever!!! Just remember to back up the Preference files too!!

Curious as to why anyone would want to? care to explain why you should?
 
No, you should not have to de-authorize your iTunes. iTunes uses your Media Access Control (mac) address to determine authorization. Upgrading to Snow Leopard is not going to change that address. Changing your logic board would change that address. Hope that helps.
 
just via dragging and dropping the iTunes folder to the home directory of the system drive from my external backup, after update the software...

So let's say I wanted to keep an iPhoto library, iTunes library, and a few files off my Mac. I have a PC acting as a server, so could I drag the folders there, and grab them off afterwards if I did a clean install? Stupid question, I know. Sorry. :p
 
So let's say I wanted to keep an iPhoto library, iTunes library, and a few files off my Mac. I have a PC acting as a server, so could I drag the folders there, and grab them off afterwards if I did a clean install? Stupid question, I know. Sorry. :p

You can drag any of your home content to any other storage device and stow it there without any issues, just be sure to copy the relevent preference file too; as applications like to write path data to it's preference/application support folder.

In general it's all safe so long as your PC doesn't go about renaming files. Personally I would avoid the PC and use an external NAS or FW/USB HD, it's just less hassle. TM is good but not 100% error free!!
 
Would an iPod video work? It's synced up to my iTunes account right now, but I could just use it as an external disc until I upgrade, correct?

It would work, as long as the iPod is big enough to hold everything. You'd have to put a copy of your iTunes on there as well, since iTunes will want to erase the iPod before syncing.
 
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