Precisely, he's homeless, but my take on that is different.
Asking for food/hot drink etc and shelter all fine.
Asking someone to fund chasing a dream of a scratch card win and to enable an ongoing alcohol problem, not OK, however tempting it is to want to feel good to think we have made them happy albeit for a very brief amount of time.
There was a time I called 111 for assistance because a homeless person (who was part of a couple who had taken up residence in the grounds of the offices I worked in) was being very sick noisily for hours and barely had the strength to stand. Within 10 minutes there was an ambulance and a police car on site. The homeless person refused all assistance other than the check-up while sat in the ambulance, but I was told that both her and her partner asked repeatedly for several different strong pain relief drugs.
The police officer who came to speak to me said that both of them were known to both the social and emergency services but would not accept the help offered by either. I then voiced concerns that winter was approaching and they're living rough, only to be told that between the various services/charities there were enough beds in shelters in our local area for those that needed them but this pair, along with many others would not accept the basic rules of no drinking/drug-taking in the shelters/hostels so would not use them or had been excluded for the night for fighting or breaking the no drink/drugs rule.
I was also duped by a homeless person asking for change because he was 50p short of what he needed for a hot pasty. It seemed so specific so i gave him 50p and another £2 for a hot drink, only for him to instantly run off away from the pasty shop towards the pedestrian underpass most people avoid because of drug dealing/taking.
I don't even give them change now, it's food/drink/hot drink or nothing.