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No worries, I actually didn't get that impression of you but I see that sort of sentiment a lot, so I suppose I was just trying to get ahead of it. I'm sorry if I was accusatory in my wording.
I agree it's absolutely a great thing to address a need, even if it's a simple comfort item. My concern just comes in with the "I'll give you this but not money because you'll just buy drugs" mentality that is so prevalent.
In a perfect world, maybe. I'd like to believe this, but I don't. Do you really trust a shelter to solve this problem for that specific person? I don't, but I can trust the $5 will go to whatever immediate need that person has. At some level, it's also a sort of marketing problem. Not many people are doing that donation to the shelter, because they don't see it. But you can plainly see the homeless person on the street corner in obvious need, and you can affect them specifically and immediately.
I have to say, at least where I'm at in America, this is a non-issue. We are a digital society, homeless included. I've rarely encountered someone who can't take a digital donation. Everyone has cash app, even if they have to take their phone to a McDonald's Wi-Fi to access it. Barring that, I could likely get cash back anywhere I could get a coffee. And we all know how inefficient a coffee purchase can be.
Sure, use your judgement. I do make a distinction between panhandling and busking, or worst of all, common street scams.
But do you really think someone would be panhandling if they had access to a better option? If you're able to inch them closer to the more comfortable life that you enjoy, why does anything else even matter?