Lil,remember he caused this by quitting his job. If he is depressed and scared he would be best served by a mental health professional. You cant solve his mental health problems. You are smart, but this is not your field of speciality.
My guess is, now that he quit his job, he is about to hit you up for money. He caused the problem, but probably will sell you a sad story to melt your heart. Just be prepared to hear it and how you will respond. Always good to be prepared.
If he wanted to address his mental health issues, how can a lawyer help him, even his mom?
He needs in my opinion to learn to help his own issues and stop quitting jobs and then panicking and asking for money. Bet he'll blame it on his roommates or girlfriend. But, really, he let them move in. He needs help teaching him life skills. You and jabber could be his life coaches, but he wont listen to you. He really really needs to hear from somebody not so involved how to do this thing called life.
None of us can live forever. All d cs will eventually NEED to do life alone.
Hugs and more hugs.