ITunes account for a minor - migrating purchases from my iTunes account

For years, we have managed our kids iPod Touch / iPhone with an adult's iTunes account.  Originally, our (now) 13 yr old had the Touch, then gave that to his brother when he got a hand-me-down iPhone.  We decided to manage their devices and purchases with my wife's iTunes account.
Now that our son is 13 (the earliest a child can have an iTunes account, I believe), we are interested in setting him up this way and either have him purchase iTunes gift cards to manage his purchases, and/or using the allowance feature.
First question: how can we transfer all the many purchases (mostly free apps, but a good number of paid apps, movies and TV shows) from my wife's iTunes account to his yet-to-be created account?
Second question: my son tells me that whenever he syncs his iPhone to iTunes on his netbook, that he loses all his games data (Angry Birds, etc) and therefore doesn't want to back it up.  I know we need sync/backup more often than we do.  What can we do to prevent the data loss?  And does this happen because of the shared account?  Or because he originally had his apps, etc on the Touch?

iTunes music and apps don't have DRM protection anymore (not sure about the movies, but it might be the same thing), so this should be relatively simple.
One way is to copy your iTunes Media folder, say on a CD or over your home network.  Have your son log in to the computer and "import" the media into iTunes.  He will be able to use the media, but it won't show up in the "purchase history" on your son's account, since he didn't actually purchase it.  So for now, it may not work over "iCloud" and he may need to physically sync the phone.
As far as the lost game data, to my knowledge that should not be happening when he simply "synchronizes" the phone. Is it possible that he's "Restoring" the phone instead of synchronizing it?

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