How do I manage two apple ids and iCloud for my teen's iPad?

Before my son turned 13, he used my Apple ID to set up his purchases for his first iPad.  Now he has his own apple ID.  He has his own iPhone and a different iPad for school.  The school wants him to use iCloud to back up everything. 
I just set up iCloud but it wants to back up the items from my ID only.  How do I get it to back up from his ID too? 
How can I even figure out which items are linked to his Apple ID and which ones are linked to my Apple ID? 
For next school year, I want everything to work with his ID, not mine.  I wish I had just made him one in his name when he was 12!
I'm not so worried about the apps, photos, etc.  I am more concerned about his documents from Pages, Keynote, iBooks... I think when he does his schoolwork it is saving to my Apple ID and not his.
I've avoided syncing to the computers because we have 3 users with different IDs and several different devices and after a while it gets really confusing to know what belongs to whom.
I know that a lot of people are frustrated that you can't merge Apple IDs -- seems like Apple ID is built for single people and not growing families who hand down older devices to other family members.

You can see which ID he is signed into for iCloud by going to Settings>iCloud on his device(s) and viewing the ID shown next to Account.  This is the account that his documents are being store in, and the one his device is backing up to (if he is backing up to iCloud). 
While it is possible to have more than one iCloud account on a device, there are limitations to the typed of data that additional ("secondary") accounts will sync.  Only the primary account (the one listed in Settings>iCloud) can be used for photo stream, bookmarks, documents, iCloud backup and Find My iDevice.  Because of this limitation, it isn't possible to sync (or "back up") documents from iWork to more than one iCloud account.

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