Before I start, mutual respect, please. Not a hate post, all opinions are subjective.
I'm around 18, and shoot street too, but not so much.
I see street photography as "humanity in a place", focusing on action or emotion whenever I shoot street. To be honest, I really don't shoot (personally I dislike it) the common "street photography" seen nowadays with people wearing masks, smoking, throwing colored powder around, playing with prop-guns and knives and seriously funny or laughable looking edits. My shots are more on the slice of life where I happen to be, or how I perceive the emotion and symbolism of human nature within my frame. Not running around with masks and prop guns of course.
Maybe it's cause my style is heavily journalism influenced, where we can't edit unless necessary to a book of codes and ethics, and that we really want to have a picture that people will sit up and look at. Thus some of my street shots are journalistic in nature, though I sometimes tag along and play with all the stuff I said earlier, prop-guns, masks and all, but I never post these. Again, this is MY take on street photography. Don't mean to say that the "street photography" said earlier is bad, I have seen good shots too.
WRT tips, I find that asking people you're gonna shoot helps. Really, just ask. It got me a few nice shots. But if you're shooting moving targets, just shoot hard and fast. TBH I've only encountered people who asks you to delete your shot only three times. And if you treat them respectably and nicely, you can make a few friends or avert an interesting situation. A street shoot got me a friend who asked me to delete, but after persuading her, she relented, and we're now friends. From my other friends who do street, their experience is that they get the most trouble from middle-aged people or from Caucasians, in which try to AVOID creating a scene.
Other tips: I did study law as one of my Polytechnic modules, and it is permissible to shoot outside, as the streets are defined as "Public Space", What happens on the streets, public places, in open view, are NOT intrusions in which a person enjoys a reasonable expectation of privacy.
I do shoot using fast primes, but I prefer zoom lens. Personal preference, but at night, fast primes are the killers. I don't always shoot B&W for reasons, its personal preference.
Shooting emotion is really great too, I was also doing some reading on Henri-Cartier Bresson some time back, and I really got influenced by him some.
DON'T wander around private property like condos or landed property, really. Street photography doesen't give you the right to sneak into someone's house and shoot in there. Abandoned places like Woodneuk is okay, but if there are people there, try not to sneak in. I had a brush with the law once, let's just say I managed to escape, luckily. If it's cordoned off, don't try to sneak in, ask the watchman before you try anything. Some Enciks will let you through if you come clean and ask reasonably, and if you tell them that you're not sneaking in or something. Reading the Constitution of Singapore never hurts.
Go clean, be green. Really, some people using street photography as an excuse to shoot beautiful girls give us a bad name. Always explain your shot to the person if he stops and stares, but if he/she really is that insecure (don't know what for), then delete your photo. If you shoot pictures that may insult someone's privacy, or exposes too much skin or smth like that, don't. Unless the person is willing to be shot, and don't assume. Even if you do so accidentally, try not to use it.
A trick is shooting JPG+RAW. Sure, delete my JPG in-cam. I still have RAW. And it's easier to edit, of course.
Oh, and always anticipate your event.
Hope I've set someone thinking. Again, mutual respect-- I won't hesitate to report trolls.
