Currently Being ModeratedMay 18, 2012 2:41 PM (in response to QueueSviews)
He uses a PC.
Which Windows operating system is he running? (XP, Vista or 7?)
Currently Being ModeratedMay 20, 2012 6:33 AM (in response to QueueSviews)
You can't put song purchased apart from iTunes on iCloud unless you pay for the newly released service Apple Match.
iCloud wont hold any customer mp3 files. Match will look at songs you have on your iTune and grand access to the matched iTune store version like if you purchased it. You will be able to share/listen matched songs on all devise using this Apple ID.