My instinct here is to want to help, but there are some red-flags that I think could do with a better explanation. While even criminals and drug abusers don't deserve to be homeless and hungry, understanding the reality of this person's situation might help to figure out the best way to help him. Here are some questions:

• He made a deal to couch surf for $300/month, but the homeowner changed her mind. What was the reason for the change of mind?
  
• He has no credit history and doesn't drive. How old is this person?
  
• No drug addictions. Is alcohol a problem?
  
• No family members are willing to help. I understand that the mother has mental issues, but what about everyone else? Father, grandparents, siblings, aunts/uncles?
  

My over-all feeling is that there is a big part of this story that is being left-out. That there is an underlying issue with this person that is keeping him from re-gaining his independence. Maybe it's not all his fault, but understanding what the real problem is, is going to be key to getting him in a better place. If he has mental issues and/or alcohol problems, those issues need to be part of the plan. Doesn't make him a bad person, but it's important to know. It's also really important to know why the family has severed him. That's a pretty drastic thing to happen and I think that story needs to be told. The family might have good reasons to do so, or maybe not. But it's very relevant.

All that aside, if I was to just offer my suggestions for help, here's my best:

• His underlying mental/physical/whatever conditions need to have a plan for support, treatment, or improvement. But this might be contingent upon getting medical or financial aid first. But even before that happens, the plan still needs to be drafted and accepted by this person. If it's alcohol, then he needs to accept that issue and plan to go to rehab or an outpatient service of some kind or even attend weekly AA meetings or whatever. If mental issues, then plan on seeing a psychiatrist or therapist. Get one lined-up and ready to go as soon as the health insurance or financial assistance begins.
  
• The family situation needs to be brought to light. Finding some resolution there will be very important to his long-term progress. He needs some family allies who are willing to help him as long as he's taking the right steps to get back on his feet. So he needs to find a way to meet with them and do some repair work. While he's getting back on his feet, there is a good chance for relapse. If he has some family available to help him thru a rough patch, he might not fall into the same hole again.
  
• His employment history and skill set doesn't sound very good, or at least he will be suffering from a lot of competition and low-wages. But this can be improved-upon. I generally recommend that people in his position make an effort to hone their resume and interviewing skills so that they can increase their chances of landing any kind of job. This can be accomplished by working with someone who has a good knowledge of the interview process and how to structure a resume. Sort of a job coach. Not knowing how to do something isn't always a problem. If the interviewer likes the candidate's personality, they are often willing to train them on everything they need to know. But while he is working on his interview skills, he's also going to need to start planning a career path. This means evaluating his skills, determining his personality type, and finding out what he has in mind for the future of his career. Once decided on a path or two, he will need to get some books and actively start studying again.
  
• His immediate shelter needs are a tough one. With no money, no friends, no family, he's really not going to have a lot of chances for an easy solution here. What he should be doing first is completely exhausting his options with family. This might mean a big blow to his ego, making a lot of apologies and promises, and frankly begging. Getting to stay with family is hands-down his best option available, and the most likely to actually come thru. If that fails, and friends arn't an option, he should be looking for a room for rent. Sometimes a small single room can be like $300/month. I don't know any places in particular, but try Craigslist.
  
• If he's going to be getting a new job, then he needs some new clean clothes. Set aside a budget (even if the money isn't there) for 5 pairs of work clothes suitable to his most likely job. Maybe it's office clothes, maybe it's physical labor clothes. Most of this can be gotten at Goodwill for very cheap.
  

I guess it's very easy to sit-back and preach all this about what needs to be done but if I don't nut-up I better shut-up. So here is what I would be willing to do to help:

• first-off, I'm not willing to give any money or provide a place to stay, do laundry, sleep, or visit.
  
• I would be happy to meet with him on a weekend (this weekend if you like) to go over some plans for his career and sharpening his interview and resume skills. I can offer a lot of suggestions on how to greatly improve his chances of landing a job. I'll take him out to eat to knock-off a meal somewhere. It would be nice if you could come too, maybe give him a ride to meet me half-way. (Between Bethel and Norwalk)
• If he doesn't have one already, I can scrounge up a computer for him. I probably have an old laptop or at the least a desktop computer lying around. Wherever he is, he will need a computer to job hunt, work on his resume, and setup interviews.
  
• We can discuss what he has available for his work wardrobe. I might be willing to get him a new shirt/pants/socks/shoes so he can pass an interview.

So that's about the best I can do. If you want to meet up, send me a PM of when he would be available to meet over lunch.