I'm a housing officer in a large (Sq mileage) rural area. We've never had a problem with rough sleeping really until this year when the figures have gone from a handful to around 50 at any one time.
However, every single one of these people is "known to service's". Almost all are excluded from the housing register due to anti social behaviour, massive rent debts etc. Most have been through the system time and time again, none of the local supported housing will take them in anymore.
That said, they all know where to come for help, and there IS still help that we can give. A handful have been in, and we're given a space in a hostel. None of them slept there. There are empty beds in the hostel, they all know about them, but they don't use them.
There are a few distinct groups, I can only think it's like a family group to them. They gather in their specific areas and drink, take drugs and sleep.
Theres only so much money and resources you can throw away. Particularly when you have families with children, medical issues etc also in need of help.