I don't know the answer but I would say even if it wasn't a problem to do both under your account you should do his own under his own account just to avoid any mix ups, confusion, or the possible trouble shooting issues involved.
I myself am NOT a fan of download games and will always pay more to have a disk in my hand. having a disk in hand guarantees you wont have issues in the future with keys that stop working or key use limits and such. even if it might be rare I often see the occasional post of "help! my download key quit working" and those people often are left having to rebuy the game again
just my 2 cents
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