While I want to be sympathetic, I have become wary. I went to university in Bath, lots of beggars and Big Issue sellers. I was a pretty skint student, but I gave money when I could. One evening I was approached by someone in the town centre saying they needed some money to get into the shelter for the night. It was getting dark, so I gave them all the change I had, three or four times what they said they needed. 10 minutes later I rounded a corner a short way off and saw the same chap giving the same story to someone else.
Maybe he was going to a shelter, maybe not. Either way, he was getting what he could from who he could while he could. It left a sour taste for me, I felt I had been taken for a fool and from that day I have disbelieved everything I am told by people on the street asking for money. Subsequent experiences have tended to reinforce this.
The number of beggars has been going up, or at least I have seen them in places were there used not to be any. Walking down my local high street I stopped to talk to a young man sitting on the pavement. It was last winter, and snow was forecast. He said that he wanted to get to Milton Keynes, that there were more shelters there. I didn't have my car and wasn't planning to go anywhere near the station, but offered to walk with him and buy him a ticket. He looked suddenly uncomfortable and said he was waiting for someone who would be there any minute and who had said they would bring him a sleeping bag. I told him I had some errands and would be back in 20-30 minutes, if he still wanted to go. 25 minutes later, there was nothing to been seen of him except his old paper coffee cup. Guess he didn't really want to go to the shelter in MK as much as he said.
I don't know what order of events sees people wind up on the street. Bad choices seems like the biggest blanket reason, one hears that quite a lot of men end up there after divorce. I know there can be bad luck, but I used to live with an alcoholic with some temper issues and he seemed to have more than his share of bad luck, but nearly all could be traced to his own bad choices. Bad choices would be made, and then sit, waiting for a chance occurrence to burst forth and cause trouble. Sometimes it would take months, other choices kept costing for years, compounding on any future dodgy decisions.
Hard to stop digging when in a hole if you don't recognise that the whole is of your own making.