Spending more on something is a good way to get more of it when exporters are ready and willing to meet the demand. Municipalities buying their local homeless bus tickets is just one example. If we want to reduce homelessness, we need a smarter approach than giving people goods and services for being homeless. I don't have all the answers here, but I do know that this requires both positive and negative incentives. A carrot and stick approach if you will. Sad to say, most vagrants are not capable of acting in their own rational self-interest, so simply extolling the virtues of becoming a productive member of society just isn't going to cut it.