I have a family member who practiced criminal defence law for a number of years, and did a good amount of public defender work helping people struggling with addictions, repeat offenders who might be classified as street people. Through having several conversations about what these people went through, I came to realize that for a lot of people in that position, there's significant trauma, often abuse that has been internalised for years. For a lot of these people, it's easier to be in and out of the system and stay in the addiction cycle than to try and face that trauma.

I'm not saying it's right, and I don't have a solution for it, but I'm just offering my 2c from experiences that have led to me having more understanding.