I live in Philadelphia, and as I'm sure other Philadelpians here can vouch for, the Homeless have it rough. There are a lot of shelters here to my knowledge, but in all of them there's a llist of things like people robbing each other, rapes, and other horrible things. Yeah, they exist, but they aren't the safest.
I personally give food every time I can. One time, I was on South Street (famous merchant street here) and there was a guy outside of McDonald's saying he needed money for food. he went on and on about how he was starving, but I felt he was full of shiat. Whatever, I thought. I got more money for my Dreamcast UFC trade-in then I thought I'd get, so I figure why not be charitable with the money I didn't think I'd have. Well I take him into McDonald's - all the while he's insisting that he doesn't want to hold me up and that he'll just take the money - and we get there to the cashier. I ask him what he wants and he goes "uhh.... I guess I'll just have some fries." HAH! From a guy who's starving. This guy was bold. He asked if he could have my change and I told him to shaq-fu off.
Another time I was at KFC and this guy walked up to my car asking if he could have money for something to eat. We went inside, I asked him what he wanted and he asked for a value meal. "Nothing to expensive" he tells me, so I respond with "Get anything you want." He does, and I mean... right in front of me, he DEVOURS it. This guy was legitimately starving. We sat and talked for a good 15 minutes, and he told me about his life,. I asked him why - him seeming like a fairly intelligent person - he was out there, and he told me that he moved to Philly with a woman, she kicked him out and pretty much left him with the clothes on his back and nothing else. She left town and left him, and he was stranded; no friends, no family. I asked him why he didn't have a job and he said that no one really wanted anyone without an address and a working shower, and that he had very unfriendly experiences at the shelter.
You have to remember, homeless people are as varied as gamers. Sure, some people are drunks and druggies, but some are genuinely good people who've come across tough times. And regardless of where your tax dollars are spent, it isn't always going exactly where it's needed.
There's my two cents.