I'm not judging here, but how did he become/remain homeless? I understand some people have issues with addictions and can't be helped, but was it not possible to help him out with money or putting him up at your place?
There was an article a while ago about a mother who was urging people not to help her homeless son (who was a drug addict), as any help given would just keep him on the streets still using drugs. Was it that type of scenario?
OK. I accept, you are not judging, so, I will answer and TRY not to become annoyed.
You need to understand, this has been going on since he was 18, he is now 43 (44 this year), so, my memory of when and how long is not perfect.
My son first became homeless, at age 18, when, although I was giving him the money for his rent (at that time he lived approximately 100 miles from me), he was spending the money on other things, his landlord evicted him.
Initially, he refused to move, the area where I lived, but, eventually, he did "move", and lived at with me for several months. During this period he failed to look for work/ training/education. He spent his days in bed, and his nights (ie say 20:00 - 04:00) "out" doing goodness knows what. He received benefits, I do not know how much. He contributed nothing to the household, except a pile of dirty washing. As I think you may imagine, this did lead to some household friction.
Eventually, it was agreed he would move into his "own" place. I gave him every assistance to do this, including paying bond, first months rent (until housing benefit kicked in), etc. After about six months of abusing the accommodation (ie not clearing rubbish, not cleaning kitchen, etc etc, he was evicted. A period of being "homeless" ensued, ie, either sleeping on a friends floor, or, a shop doorway, or, sometimes a hostel. This cycle continued several times over the next few years, until he was aged about 32. I was interspersed with a spell in prison for possession of a significant amount of "weed". (I do not know how much, he said that it belonged to a "friend").
After he emerged from prison, I found him "bed and breakfast" accommodation, in a pub. The landlady of the pub was a no nonsense character, this resulted in a period of relative "normality", which lasted for about 12 months. Housing benefit paid his rent, he had benefit money and "earned" a bit "cash in hand" doing odd jobs, running errands etc. This halcyon spell came to an end when he allowed some of his shady "friends" onto the premises, out of hours. Let us just say, unacceptable things happened. The Landlady did not turf him out on the first occasion, but, by the third time, she had had enough and he was given his marching orders.
Another spell of 6-12 months "homeless, and sofa surfing".
Somehow, goodness knows how, during this period, he met a "girlfriend". More resources and attending meetings with local authority housing department, on my part, with my son and partner also in attendance, and they were allocated a council flat.
This was almost a "success" it lasted for about four years, before they were evicted (yes, none payment of rent and council tax), with arrears of approximately £1500.
Another period of "sofa surfing", followed by another Council Flat (single), evicted again after about two years, yes, you guessed it, none payment of rent.
At present, he is living in a very shoddy (private) flat, with another partner, rent paid via housing benefit etc. So far, this latest "round" has lasted for 8 months.
He is 43, his partner is 44. Neither of them have worked a day in their lives.
Forgive me, but, I am not optimistic.
If only it were so easy as throwing some money and few bags of groceries at the problem!