Jaffacake2 I used to take in homeless people and help them get back on their feet, but now I run a homelessness charity so I need to maintain professional boundaries.
I never give money to homeless people locally because my charity provides anything they may need; boots, clothing, camping equipment, hot meals - whatever will keep them warm and safe and well. We also provide additional long-term support to assist them to access whatever further help is needed.
I would never say don’t give money to people on the street, but wisdom is needed. If someone is misusing drugs I suspect you really won’t want to discover it was your money that funded an overdose. I was recently contacted by someone who was upset at finding that their ‘good deed’ of giving cash had resulted in the near death of a homeless person.
Outside of my own town if I come across a homeless person I always stop and offer to buy them a meal or a hot drink. I used to carry several pairs of new socks with me and small tubes of toothpaste, but I haven’t replenished my stocks during COVID. (New socks are a really welcome gift for people who are genuinely homeless - I once had a lovely lodger who bought a case of them to hand out, I think it was 144 pairs!)