And now I'm back around and it's late after a long day at work, so a pre-warning this will possibly be incoherent and rambling but hopefully it will some sense.
I definitely don't have much in the way of hard answers (lots of anecdotal evidence to support my ideas though), but happy to have the conversation either here in the thread or by PM if you want some specific questions discussed... Some background I've been working for the past 5 years at Mobile Loaves & Fishes both with the Food Trucks and as one of the property managers at Community First Village
To start there's a few different types of homelessness you might see:
1) Transitory: Something happened and shit fell apart but it's probably not going to stick and within 3 months things usually are on the up and up. This is usually the easiest to assist, and the system does a decent job at serving and helping these folks transition out of homelessness. Occasionally if during this time more issues happen (addiction, physical or mental health degradation, criminal activity) then it can transition into one of the next two.
2) Episodic: Usually tied to mental health or addiction issues. You'll see this population cycling in and out of rehabs and similar programs. A good number of these folks end up in supportive housing communities like Community First! Village. If they lose the social connections because of this cycle it's usually what leads thing to the third type.
3) Chronic Homelessness: a year or more on the street consecutively, or multiple episodes adding up to a year in the past 3 years or less. These are often people who have degraded social connections completely (family, friends, church communities etc) either by the own actions or by outside circumstances. We believe that this catastrophic loss of family and community is the root cause of this type of homelessness. Maybe the instigating circumstance would have been bad enough to create transitory or episodic homelessness, but without people to turn to and to rely on when things are going to shit, it becomes a increasing feedback loop of ostracization and departure from the normal social structures which further ingrain the issues that got them there in the first place.
Chronic homelessness is most of what you see encamped around the ARCH and it's the hardest to break out of, because most programs/individuals are maybe willing to throw money out there to feed/clothe. That's very good and important (it's been MLF's bread and butter for 20 years). Maybe a step up from that is getting people into housing or work. Thats even better than the first option and it works for some people (mostly those in Transitory or Episodic homelessness) however often it's much more expensive than an individual or private community (like a church) can sustain outside of single cases, and it's not very effective for Chronic homelessness (about 25% - 30% effectiveness is the absolute best that I've seen), because it's often predicated in taking an ostracized and outcast person (for whatever myriad of reasons) and putting a roof over their head and assuming that the rest will follow, but their still an ostracized person with all of the same myriad of reasons and most of the time still without any community or social structures. Work if it is available at all often requires consistent transportation, figuring out the healthcare system on your own is a nightmare and try it without insurance, Without that support and exchange of humanity (that we take for granted) it more often than not ends up being expensive temporary shelter rather that further fucks their record (with evictions and collections). It's not impossible I've seen some ASTOUNDING success stories through that model, but it's not resolving the issue that you encountered. It's a better bandage but it's still working on the wounds at the surface, we have to go deeper. People who are fantastically and traumatically abused and hurting don't just need a roof and four walls, they need someone to care about them and someone they can care back about. If there isn't purpose and relationship in people's lives then struggles
What we do at Community First! Village is try to go upstream and address that root cause of lost community by making it the forefront of what we offer. We get people into housing, we provide good dignified well paying work onsite in everything from woodworking to catering to blacksmithing to farming and on and on, mental and physical health as well addiction recovery resources are on site and free. More importantly we flood the community with relationships. The houses are built in a orientation to encourage and foster relationship, volunteers come out to the village by the droves and are lead in their work by the residents which not only builds up that person but breaks down the stereotypes people who volunteer bring with them about what being "a homeless person" mean. We setup a community council system the neighbors to elect representation that comes to the table with staff to make changes to better the community. We're 3.5 years into having residency out here and we have 85% retention or positive transition without relapse. We're already even building 300 more homes to be finished and ready for move in next year, and are pursuing options to expand to over 1000 residences if possible. I'll be the first to admit t's not perfect, but it's definitely a new approach thats working. Don't just take my word for it though, if you spend a day volunteering or even just coming to an event out at the village you'll see the difference community makes. Most of the people you see thriving at the village were not long ago the same people you saw languishing outside the ARCH or flying a sign panhandling on the street corner.
Anyways I'll give it a rest, and answer questions, but I wanted to briefly respond to the OP's original set of questions, because I appreciate his willingness to listen to the person that he met and actually take some energy to think about the issues brought up. In a world of people not giving a shit about each other, you did and that means a whole lot, so thank you.