Besides, I wouldn't feel right paying him $100 and then using the piece in a manner we hadn't agreed to for that price
No, you want to not pay him the $100.I wasnt saying that. What I was saying is that atm for the corperate image, it is just as wrong to make your own version of his image, as it would be to pay him $100 and then make your own version of his image.
But morraly its better to pay him $100. Obviously this will change it you sign a contract.