If those are the actual numbers, you're proving GP's point. You can give each of those 14.5k people ~$55-60k instead of giving 8k people $100k and homelessness is still solved.
They had homes, cardboard box homes. Then the government said a home couldn't be a cardboard box, and confiscated the cardboard boxes and now they sleep on benches.
It's unlikely there's a trivial arbitrage to eliminate homelessness in a city full of engineers.