Opinionated opinions follow.
My only problem with this is that you never know if a person is legitimately homeless or not. It's easy to grab an old bookbag, some shabby, oversized clothes, and a moth eaten blanket and set yourself up on the side of the road. A little olive oil in the hair with some purposely made knots and it'll look like you haven't had a shower for weeks. For guys, just don't shave for a while or shave half-assed and you'll look just like a homeless guy. Then, sit around by a train station or by a bus stop and look sad for a while. Come up with a decent story to explain your situation without being over-the-top about it, and shabalang, plenty of suckers passing by will give you money or buy you something (especially if you're particularly young or fairly old).
It's so easy to lie that it's hard to take people seriously :L On one hand, some people think you should be generous whether or not they're having a tough time and help them anyway. But on the other hand, that's your hard earned money; why would you give it over to someone who might just be faking homelessness?
Not trying to be rude, but as far as I know, there are plenty of shelters in and just out of the city. There's no need to be sleeping on the streets. You can stay in a shelter until you can find a job. I admit, it's not always that easy, and we went through this while my brother was homeless for a while (neither us nor his friends would take him in, and he had no job), so I know that getting into a shelter isn't always that easy. But it's possible and reasonable. I can't really take people sleeping on the streets seriously because of that. It's so easy for them to just put some effort into making their situation better instead of lying in the cold hoping somebody will donate to their poverty-cause.
>>8 point of the Missions board*