But does it scale? Once you get beggars knowing they can get free money like this, how much do their attitudes change? How many people start to scam the new system? Does the scamming effectively prevent it from helping people who actually need it?
And as pointed out in other comments, many 'homeless' are homeless by choice, not because they can't get one. Some beggars aren't even homeless... They just choose to ask for money instead of earning it.
It's very difficult to make a system work properly when all humans are involved.
Yeah, people will either go along with a game plan or game the system itself. But maybe this is a way to structure in some freedom and personal connection that isn't there currently.
The move to electronic benefits from paper food stamps has reduced fraud substantially, and perhaps most significantly reduced the social temptation to game the system. So it seems like there's a similar benefit possible from moving from hard currency panhandling through rechargeable gift cards and public-purchase credit cards.
If a Kiva-ish system is more beneficial than standing out on the street, maybe you give people the freedom to stop structuring their life around panhandling and give them incentives to live more independently.
And these tools could even help provide a system that actually fills the gap between someone just making it in the working world and giving up on it for the more toxic world of panhandling.
But it's true that you are facing the most enormous incentives to game the system imaginable. It requires some really careful and clever reward design. I know it seems a little overenthusiastic, but I keep thinking it would be fascinating if there were a nonprofit that offered game design resources to other nonprofits...
And as pointed out in other comments, many 'homeless' are homeless by choice, not because they can't get one. Some beggars aren't even homeless... They just choose to ask for money instead of earning it.
It's very difficult to make a system work properly when all humans are involved.