I don't think you're being mean at all, if I am reading this all right, he is perfectly happy with your choices for him (or lack thereof).
It does remind me of a discipline issue we had with my son. He decided to be spoiled and snotty (not that I think your son is, I see there is a much different issue there), so when he got home from school we told him he had been striped of all privileges and no longer owned anything but the clothes on his back. He was presented with an "inventory" of his stuff and activities which he had to earn back with good notes from school and chores at home. U