Okay brief summary on the projects:

A friend was long term unemployed and because I knew that he was ok with math offered my co-founder of the startup I was involved with at the time to "hire" him for intensive training. The idea was - he was payed to study and to write unit tests after that for our code. We payed the guy subsitance rate - so pretty small financial approach and helped him with the studies. So after 3 months of training he was hired on normal rate and pushed towards QA and testing automation. But after that he begun to slack a bit (mostly related to his girlfriend, spend way too much time with her and not enough on self improvement which was part of deal) so he could not keep up and we let him go. This was like a wake up call for him and he got his act together, found his next job on his own and now is making career in very respectable company with above average income as QA.

The second was a bit different - a friend of mine soon after birth found herself single and with the baby soaking up all her income and time she was unable to take care of herself which led her to depression. She was eating junk could not shed the pregnancy , couldn't bring herself to shape and her figure was greatly deformed (according to her). So I offered her a deal - I buy her all the food she needs (I wanted to see how low carb diets work in women), she does not restrict calories and just tracks every day her weight and progress. So we go to shop every day, upgraded her from starches and sugar to leaner meat, fresh produce and some fruits with the occasional bar of dark chocolate - while she did not lost much weight she is in much better shape, very vigorous now and have better figure than before. Her waist slimmed like crazy. It is ongoing btw.

Now about that project - these guys are not homeless. They are houseless if I can quote George Carlin. What they need in the first place is warm and dry place to stay, a shower, a mean and clean clothes and maybe some help with an addiction. They need that kind of a break to be able to begin turning their lives around. They also need a job. A great part of a person's self worth comes from that. That guy - I wish him all the best btw will still need to find projects and work with his new javascript skills. How exactly will he do it?

Now what I will describe is the minimum needed things for that kind of project to have a chance of happy ending (a guy from the streets to be reintegrated into the society):

1. First - make it a long term project (6 months)
2. Provide some kind of shelter and basic food security and broadband - if you are really serious about making technologist out of him 3g or LTE won't be enough
3. Make him feel worthy about himself as human being - give him tasks that produce value - give him normal linux machine show him the help and make him setup a lamp stack himself, setup his ide etc. Guide him and give him tasks that are of real use to someone - personal site etc. Enroll him in Edx and coursera - the python edx MIT course is amazing. If he happens to be a decent human being try to create leads for him when the project is over about projects jobs or show him where to look for freelance work.
4. Also have very detailed and very reasonable schedule and expected milestones and be ready to pivot at any moment - he may not have the chops for programmer but he could be great admin or tester or designer.

I know it is a lot, but I don't think anything less will do and you are just playing games with people's lives.