I've honestly found I give money to the ones who flat day they need beer money fairly often. I've also gone into a gas station where someone was asking for help and bought them a burger (I ate one too, guilty pleasure) and had lunch with them.

I agree on not judging, but I also see what Karnage is saying too. Enabling destructive behaviors is not good too. I'm glad people think on how to help the most helpfully are out there. Lazy me gets to benefit from and contribute to the things they discover.