The challenge of street is a cliche: making the mundane interesting. You can do this any number of ways. Use shadow, use the light of the early morning or an hour before dusk, find interesting people, funny moments, juxtapositions, on and on. In most street photography it is the scene/situation that is in the frame of your camera that is the subject, not the people. How much can you ever know about the life of a stranger in a photo? Next to nothing. But that is not really the point.
If you need special access then you are doing something like photojournalism.
Here's what I think could be done concerning street. A previous post mentioned getting close to the subjects.
I mentioned that seeing the homeless and photos of them became boring. Why? No connection. Sure, I agree there has to be all those things you mentioned above.
Look at it this way, you go out and you take photos of the homeless, yes they are on the streets and quite pitiful, but most people either walk past them and gruffly say "get a job" or feel a sense of fleeting pity until the next thing captures their attention. That's just how it is on the streets of a big city.
But if you, the street shooter, get a little information about Jeremiah Jenkins "homeless guy" then you might have something of interest. He'd might tell you that he was released to the streets via deinstitutionalization of the mentally ill if he's not "too off in the head". One day he was enjoying three hots and a cot, the warmth of being indoors, clean clothes, etc. The next day he is free to go due to the hard fought efforts of an unknown to him entity fighting for his civil rights. How's that for irony?
What about rolling up on a group of young people behind New York's Bellevue Hospital, or Bronx Lebanon or Downstate Medical Center at 2AM. Bellevue is a big grimy city hospital that has a Psych and prison ward that everybody thinks of when the hear the name. The others are similar.
You might find them out there buying a sandwich and a Snapple from a vending truck of all places. That is their wind down ritual. You'd find out that they are physicians in training recalling a case about the guy with 5 gun shot wounds they just saved (Tupac Shakur), or the reporter for a major NYC newspaper who almost died during surgery from his injuries from a car crash while driving drunk on the freeway.
They'd brashly tell you that if those patients had been taken to a brand x hospital ( a cushy, pretty, suburban hospital) they'd be in a box now. (yeah the talk that way) Or they might tell you that they are scared that they won't find a job when they finish training due to the new administration's plan for health care reform (Clintons). All the while you're clicking away ... you got no special access other than being there. Then you'd have something, a street story. You would then know a little about them (folks, most people are dying to tell you a story) and the pictures are from the street to boot.
What about the pregnant lady with the stroller carrying a toddler trying to catch a train to NYC from NJ. She has a distressed look on her face and you find out that she's anxious that she won't get a seat because men always beat her to them. So she rides the train standing up for 40 minutes trying handle the toddler. But when she gets into the city, people will more than accommodate her on the subway trains going to her destination.
People in the mean city are nicer than suburbanites? You might also find out that she is concerned about childcare for the baby when he comes. Her maternity leave is 8 weeks but the day care won't take the baby until he is a least 12 weeks old. Of course you ask her if you can take her photo and she agrees. Again this is happening on the street.
Is this PJ, I don't know. You're certainly getting a story and pictures, but it does take only a tiny bit of time, it's on the streets ... but it's quality.
