Hi;
It sounds to me like he really knows what he wants to do, it's just a matter of how to get it done. The emptiness he is feeling may be a part of his not being able to finish his schooling. If the female tenant is causing him trouble then it is best to get her out of the picture.

In order to get himself back into a positive outlook he should start back on his exersize program. I know for myself that being able to hike and camp out are great stress relievers for me and a way for me to get closer to nature and spiritual things.
Eating right and cutting out alcohol, or at least reducing the intake of it will help tremendously. Alcohol can be a depressant and is not really good for the body. I do indulge so I'm not advocating teetotaling, just cutting back for a while.

It is good to cry, it is the way the body cleanses itself of stress and can help center our thoughts and clear our troubles.

Good luck yo your son, he is young and although the job market is bleak he can make it, give him a copy of Think and grow Rich by Napolian Hill. A great read and encouragement especially in these hard job market times.

Eric