If John does any programming (you mentioned he knows a lot of technical stuff) has he tried doing freelnace work through sites like rent-a-coder? What sort of tech stuff does he know and like to do?

Hmmm, the kitties may hafta start taking freelance work - "Need your clothes decorated with cat fur? Want to learn how to truly nap? Need a little fish-breath in your life? Want a real-life black cat for your Halloween party decor? Rent-a-Cat! email [email protected]!"