Sorry I didn't get a chance to see you Anna. Angelo and I were dead tired, and didn't know how it would go at the Consulate; luckily, it actually went very well. I took in his documents, and although they listed the passport of a parent as a requisite, they didn't even ask for it. He turned in his old passport, a copy of his birth certificate, paid $115 USD, and we were told these passports are now sent to New York to be processed, and should be ready within 1-2 weeks.
I decided to try to talk to CIC (Citizenship Canada) again. I told them that I had a Court Order stating that I could make Angelo a citizen of Canada. They asked me several questions, and told me that in my situation, I should apply, surely Angelo would indeed qualify! That makes me very happy, so now to wait for the passport and send away the application. Hopefully all will go well, and in due time, Angelo will have his Citizenship!