ITunes recovery and repair

I posted this on the 'using iTunes" list and thought this might be a better place to ask. Sorry for the cross post.
I don't have an iPod and don't use iTunes, but as part of my prepunishment and preparation for 'ell, (you probably can't say "h'll" over here either) people have been bothering me with their computer problems for decades. I'd have two cases that an iTunes expert may be able to help me with. Both clients make Homer Simpson look like Einstein and stand no chance of fixing things themselves, no matter how much tech support they get.
1. XP laptop so riddled with garbage that it takes almost 20 minutes to boot. It's way too diseased and corrupted to use at all, or even think about fixing. Re-install time. Using a Linux boot CD, I've zipped up all the user's files including the My Documents/My Music/iTunes. Is fixing this a simple matter of re-installing iTunes and restoring the My Music/iTunes directory?
2. XP desktop. Runs fine, but My Music/iTunes is heavily corrupted by a hopelessly naive user who moved iTunes, copied it, zipped it up, unzipped it, and left so many copies of it lying around that it's hard to tell which one iTunes is actually using. Though I am sure that it's no longer the normal My Music/iTunes location. All of this was done trying to copy wmv files ripped with Windows Media Player into iTunes. After ten years, this guy can't fetch pictures off his camera without help.
Amazingly, iTunes still works fine. But he's replacing the XP machine with another, so this needs to migrate to the new machine. He also bought a Mac laptop and may want to run iTunes there instead. Because of the mess he made, copying the iTunes folder is at best, an very unattractive option.
In both cases, I'd like to preserve the music these folks bought from Apple. What's the best way to do this? Is there a way to re-fetch all the stuff you've already purchased from Apple? Any help would be appreciated.

The recovery partition is not updated by the Windows 8.1 upgrade. So it produces the same recovery media.
Upshot is that when you recover that way, it restores the hard disk to its original out-of-the-box contents with Windows 8.0.
-Jerry

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