That reason may just be that it is a cute 2 bedroom duplex on the edge of a C class neighborhood (this would be ok)... or it could be because only homeless people want to live on the street (this would be a nightmare.)Interview Contractors in advance.

If I ever make it I wanna work with the homeless in some capacity .

Our suburban Chicago community has so many members we've outgrown our meeting place (where we've been since BEFORE the crash), has weekly study groups to help people understand what they are learning and monthly all-day workshops where one of the instructors from our classes (I believe we are up to 20 instructors now, 49 classes totalling about 500 hours of on-line material available 24/7) comes out and teaches without selling anything.We have other communities around the country, as well.If that's "too good to be true", then good luck to you.One couple in our community just finished a 32-unit project (in four buildings) providing housing for homeless veterans: rents guaranteed by the VA.

It is my goal to provide housing and a support system for foster children who have aged out of the system and have found themselves homeless and destitute.  

The owner had been collecting clothes for years, to give to the homeless and different shelters.

Frustrated with the system and the homeless rates of former foster youth, I developed my own program to improve those outcomes.

When I was in NYC, I spent a few months in a homeless shelter surrounded by violence, pain, mental illness, theft and deplorable living conditions everywhere you turned.

We also have a tenant who is a recovering alcoholic and formerly homeless who needed a solid place to get away from family and "friends" that were enabling past behavior.  

The wacky homeless folks that hang around your block are interesting or colorful when you are a carefree 23 year old...

The other two options: Cash for Keys (which you tried once... try again) and Services for the Homeless/Social Service Agency Guidance (provide a list of resources in your area in which he may engage.)