Thanks for the responses, I appreciate your time very much.

Firstly, I have his first and last name, his mother's first and last name, as well as his exact address (via iOS 'find friends').

Secondly, (re: second responder) I'm definitely in CYA mode.. I don't feel good about it.. Be I had to start recording everything when the issues first became apparent.

Thirdly, he lives in Canada, and I have a message out to a crisis center in his city asking for direction.

4th and so on; this is not a boy's cry for attention, nor is it a passing phase.
I know some details about his mother, I don't feel comfortable posting them here, however. After talking with him for at least 50 hours, I have spoken a bit to his mother, and have heard her pleas asking him to eat, go to bed, etc. As I expected, he pretends to obey her, but doesn't. When she tells him it's too late to be chatting and to go to bed, I explain to him that I can't enforce her rules, but I feel obligated to honor her wishes and have to end the call. I know that she is concerned about it. I believe both he and she went through some trauma involving the father.. She gave him some time to heal, and now she's really just enabling his behavior.

It's also clear he's had some counseling/therapy.. He is quick to respond to my questions with what I call 'anti-answers'. He knows how to deflect and manipulate almost everything. He gets angry when I ask a question for which he's not prepared.

When looking at the 'checklists' for bipolar disorder and depression, it's not just a few of the list items that apply, it's 99% so far.

He'll be waking up any moment now.. And proceed to try to reach me.
When he can't get me, the anger is real..

My last resort is to contact the local suicide prevention center, or something similar. I would have done so already, but I've had enough experience with crisis centers that I am certain, it's not the best option.. However, when I'm down to the 'only' option, I will.

There are so many red flags here, I feel obligated to make some effort to prevent another Columbine or similar tragedy. It would be inexcusable to brush this off and later be reading about how whatever tragedy could have been prevented if someone had just done the bare minimum.

Keep the suggestions flowing! I know for the most part how to identify the problems, even the causes.. I've even been surprisingly good at helping him without overtly trying.. I.e. Carefully thinking over every single word I'm going to say.. And letting him know that I won't abandon him. I'm trying to use myself as an example, rather than saying I know how he feels (everyone could probably guess what happens when you say that).

I'll sum this up by saying I would like help and suggestions for tactics I can use to avoid the rejection. If I can convince him to get help, it would be so much more effective than intervening on his behalf.

Thanks again for reading.