The people who are homeless with dogs are usually crusties and hipsters who want to be homeless out of choice for the experience. At least they are in NYC. I just glare at them. I don't give money to anyone. If I have fruit or water, I'll give it to them. A lot of them are full of bullshit though. I went to a Tim Hortons once and some guy came in begging for money. I told him I'd buy him a coffee and my friend offered him two oranges and he declined and said he wanted money. I told him to fuck off before I got security.  That wasn't even the first time a 'homeless' man didn't accept food from me. They're usually grifters.