Somewhere someone said that the photographer's attitude is the key to getting good street photos, as opposed to the size or obviousness of the camera, and I agree with that completely.
After spending three weeks with three other photographers and much of that time walking the streets of Myanmar, I have become very convinced of certain issues.
What I am after are pictures where the real personality of the subject comes through and not the frozen face of someone taken by surprise or reacting to the camera.
1) Using the camera as a barrier between you and the subject is deadly. The subjects sense this and they freeze. When hoping to get pictures up close, I always approach subjects with the camera down at my waist. I know what the settings are, or will need to be, and I adjust the camera before I raise it.
2) speed is crucial. Letting the camera linger at your eye also turns off the subjects because then the camera is seen as important and they start to wonder why. I raise the camera and take the picture as quickly as I can. I try to minimize the importance of the camera and the shot in my actions. I am willing to sacrifice perfect framing or exposure for the shot.
3) contact with a subject who sees you is crucial. I am not a camera with a person holding it, I am a person who has this lump of metal at his side. If I plan on taking a picture of a person who sees me, I engage them in a real manner.
Often I make faces at children and they are unused to adults interacting with them in that manner and so they are often taken aback and even delighted. It is easier for me because I am older and generally un-threatening. I will often allow the subject to first take a picture of someone else or of me and then I will take a picture of them
4) Walking with another photographer is deadly to most interactions with people. By myself, it is rare that I can't get into an interaction with someone or some group, just by showing interest in what they are doing regardless of any language barriers. Being with another photographer makes me less approachable and just doesn't work.
I got this first picture above by sitting on a low concrete wall and watching the younger girl sweep with the broom whose handle you can see. I took a picture of the street and showed it to her, then I took a picture of the storefront and then I motioned that I wanted to take a picture of her older sister. By then, she was anxious to get in the shot.
The close up of that rather fierce looking man came after I saw 4 or 5 people sitting around a low table on tiny chairs eating from a large plate filled with hot samosas in the 'Indian' market in Yangon, Myanmar. I walked over and looked intently at the food and, of course, they invited me to sit - which I did. They indicated I should take some food, I ate a samosa, indicated it was great and took a picture of the dish. Then I obviously took a picture of the group, everybody was comfortable because I had accepted their hospitality. Finally I took a picture of a man sitting across and showed it to this man sitting next to me. Then I took his picture and showed it to everyone. After I few minutes, I looked at my watch, thanked everyone, shook hands with the men, gave my card to the oldest man with proper courtesy (right hand holding card, left hand holding right elbow), stood and left. No common language spoken but a fine interaction.
Real interaction is important. Don't lead with your camera, lead with yourself.