I put my son out homeless with no car. I did go to Wal-Mart first and get him a jacket, backpack, beanie to keep his head warm, gloves, shoes, and some food items to take with him. That was my way of feeling better about the whole thing. No money ever though. I took the tags off of everything so he didn't know where I bought it.
One other time he was dangerous and I had to leave him out in the cold rain all night too drunk to help himself. I wasn't sure he would make it. The police wouldn't help me. I handed him out a sandwich and cup of coffee in the morning and sent him walking.
He never lived with me again after that. It was really hard, but we both made it.