Originally Posted by
raiven
Lol, bring cigarettes too. :) those guys generally have a territory, so if you wander around in the same area you will find him again more than likely. I like to wander in the downtown core, up and down alleys etc. If I inadvertantly come across a homeless/street person or persons I just say 'Hi How are you doing' etc. or 'good morning' and they do the same. Almost every time I go out to shoot, a street person comes along and asks me what I am doing. They are very bold in that respect. I generally do not photograph them, but most are willing to be photographed especially for a bit of coin.
Also, I would say if you are in area you consider 'rough' dress the part. Do not stand out. Carry your camera in a duffle bag or beat up looking knapsack. Treat the people you see respectfully. Do not have a look on about that says, "Oh noes I may get jumped!" If you get a bad feeling about the situation, just move on. Don't be a hero. :)