Update.
Unbelievably, we continue to correspond, and he follows my rules pretty well. I think I only forced the termination of one thread, because of a picture he sent me.
Vaya, he got my email because he knows my name and I have a public web presence.
Vale, he asked for money once. He wanted to know why I refused, but accepted my reasons without complaint, once we were clear, and hasn't brought up money again, so far.
It's ridiculous, but from his point of view, I'm pretty sure I'm an important friend. He's 35, but he's still a mixed-up drug-addled kid to me.
My big question now, is how do I tell him that if he wants to win the girl of his dreams, he should get his meth-ruined teeth fixed?