Downloading Previous Purchases?

My bosses' computer got wiped yesterday and unfortunately he has no backups of his music. I'm trying to help him out by restoring his previous purchases on iTunes but it seems I've run into a little problem... He started the download (of all the previous purchases) through the Cloud earlier today and then put the computer to sleep shortly after that. Now I have the computer and for some reason it's listing all the songs as "Downloaded" even though they are not (tried finding them in Spotlight to no avail). Since they are shown as "Downloaded", I can't start the process and redownload... anyone know how to reset this?
I already clicked "Check for Downloads" and that didn't yield anything so I'm not really sure what to do, any advice is greatly appreciated.

I started with this article: Downloading past purchases from the App Store, iBookstore, and iTunes Store, http://support.apple.com/kb/HT2519
and it referred me to this: iTunes: How to resume interrupted iTunes Store downloads, http://support.apple.com/kb/ht1725
and that ended with this: How to report an issue with Your iTunes Store purchase, http://support.apple.com/kb/HT1933
Hopefully one of these suggestions will help.

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