I'm not really in vehement disagreement with you -- I like the way you're looking at it. But, once a person has no cell phone, address, home, facilities for personal hygiene, bank account, credit, or income, getting those things with money alone is tremendously difficult. Many of them require at least one of the others. You'd end up giving them a lot more money just to get the things they need anyway.

For example, cell phones: if you have no address to send a bill to, no bank account, and no credit, what kind of options do you have for service? You're a lot better off getting access to a service designed especially for your situation.

...and, much as I'd like to sidestep this point, the reality is that a lot of homeless people don't have the best financial judgement. That's not to say they're bad people or will spend money they can't afford on drugs or alcohol (I don't think either of those is as true as most people seem to think it is), but prolonged homelessness is rarely caused by a single bad decision or stroke of poor luck.