You said "If I could be guaranteed that it would help him, I would do it in a heartbeat!"

You know that can't be guaranteed.

It is a question of possible actions and possible outcomes.

What it looks like right now is the path you are both on is heading toward disaster. He may be commited to the outcome, but why are you going along for the ride?

Ultimately, people mostly create their own destiny. Sometimes you have to let go of one's you love to let them find their own destiny and it may not include you. I have some idea of the stress in this in that I have a teen son wandering a foreign country with no job. You mentioned he might become homeless. This would not be the end of the world. It might be the needed wake up call.

I don't know.... One of the first things you are taught in first aid class is to not make more victims. In other words, when you encounter an emergency situation, take the best care of the victim you can without hurting yourself, too.

Bumper sticker: Wherever you go, there you are