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Disclaimer: All the views expressed here are mine and are not necessarily representative of other photographers, or reality. If I offend anyone, I apologize.

When Mary asked me two write a journal entry about street photography, I immediately accepted and was honored. After replying and accepting her offer, I wondered what I had just accepted. Me? Talking about what it's like to do street? What do I know? And if you happened to read one of my journal entries (When things go wrong photocolo.deviantart.com/journ…), my street photographic endeavors are not always well received. Additionally, I feel that I am in no way an expert or know tricks, or rules other don't know. But then I thought, maybe that is one of my strengths in my approach: I don't really have one.
Every subject, situation and accompanying risks are different for every street photo that is taken. Sure there are some basic very general advise that can be given (and I will do so a bit later), but I think that the best approach, and certainly the one I try to adhere to, is to be open-minded, ready for the unexpected both for photographic opportunities as well as how to handle my subjects' responses.
This opportunistic approach works well for me for several reasons. First, it keeps me from following a particular script. Scripts are great for predictable moments but street photography is by nature unpredictable. Second, it fits well with the nature of street photography: Waiting, hunting for the decisive moment. That decisive moment is very difficult to anticipate and I believe that the photographer's reaction to the subject's response should ideally be spontaneous as well. Third, it forces the photographer to analyze the value of the photographic opportunity and be ready to validate it to his or her subject.
This no-script, no-plan approach is most difficult for me when I have taken a photo that I really shouldn't have. This might be because after the fact, I realized that I went a bit too far in intruding on one's privacy, that I have captured a vulnerable moment, or simply that the urge to capture photos has made me release the shutter for no good reason. These occasions are difficult to defend and I often regret having taken these shots. But when you know the photo is good, that I captured something that was special, then it is much easier to explain my action to my subject.
Passion is something that I have for street photography and I find that expressing that passion to my subjects removes the majority of their negative feelings. How to express that passion is different for every subject (and photographer) but here are some general tips, if you desire to call them that.
1. Be friendly. Always smile as a smile by itself goes a long way in appeasing even the most reluctant subject.
2. Don't act like you have done something wrong. Assuming it is legal to photograph individuals without their consent (check your local laws), then act naturally. For example, don't try to hide your camera after having being spotted by your subject.
3. Be prepared to explain what you are doing and why you took that particular shot. This goes back to what I mentioned earlier. If your intentions were valid then a quick explanation such as "Your hat, it is just so beautiful!", or "Your purple sweater matches the purple flag", or "You just look impeccable!" gives a rational explanation for your action and if it is in fact true then your subject is likely to understand and forgive your intrusion.
4. Be willing to show the image on your camera (sorry, digital only) and offer to send it to your subject. A handy business card is never a bad idea, although I must be honest and tell you that I seldom get to hand one out.
5. In some cases, asking permission is the way to go. I personally have a difficult time requesting permission as I don't know how to direct my subject to recreate the spontaneous moment that attracted me in the first place to the subject. I know quite a few photographers who excel at that and I would love to learn from them!
6. Be prepared to delete the photo. I have been photographing street for only a bit over two years and only have had to delete two photos. Do I regret these? Yes, one in particular, but at the time, it was the right thing to do and deleting that photo is why I'm still able to photograph today, no joke!
7. Sometimes it happens that things go really wrong and you encounter mentally ill individuals (in the United States it is estimated that 26.2% of the general population suffers from a diagnosable mental disorder! That's about 57.7 million people!). In these cases, first, it is important you remain calm. A person with a mental illness might become extremely agitated or aggressive very quickly. It is imperative for you, the photographer, not to get riled up and remain calm. The person might even initiate physical contact with you. It is important for you to establish safety boundaries all the while remaining calm. Be calm but firm and request that the person not touch you or your equipment. I think that it is important not to agree to anything the individual is asking you to do, even if the request is to delete the photo. Again, if you have a very strong feeling that erasing the photo will deescalate the situation, then do so! Your priority should be to deescalate the confrontation and if needed look for help from law enforcement or medics. 

In this last section, I would like to share my personal and limited impressions about how street photography is received in the places I have visited.

New York City

Probably my very favorite place to visit and photograph its people. New Yorkers are amazing people; really I mean this. They are friendly, understanding and extremely tolerant. Taking candid shots of New Yorkers is easy, as simple as that. In general, one must go to great length to offend a New Yorker with a camera, although it certainly is possible (see Bruce Gilden, a street photographer whose in-your-face approach certainly provides fantastic results but can be deemed a bit too confrontational).

Chicago

Generally, speaking Chicago isn't unlike New York although I would say that the opportunities for street photography, especially 'people' opportunities are far fewer than in New York City. The architecture in Chicago is absolutely fantastic though!

West Africa

Ghana and Togo were the most challenging and vexing photographic experiences I encountered. As a white man, it is simply impossible to disappear in a crowd. There was ALWAYS at least one pair of eyes on me at all times. Let me share a personal experience that will make this point. I was in Accra, the capital of Ghana, in a busy market call the Kaneshi Market. The sun was setting over the market which is located inside a concrete building that resembles a parking structure where all the cars had been replaced by vendors, selling everything from local foods, to beauty products. I positioned myself in a corner of the market near a stair well as it gave me a slightly elevated view of a section of the market with many vendors selling olive oil, tomatoes, and stands full of various fruits and vegetables pilled in the shape of pyramids. Naturally, all eyes were on me and my idea at the time was to attempt to get the people used to me and ultimately forget about my presence. I fiddled with my camera pretending to adjust its various dials, raising it, looking through the viewfinder briefly and then lowering it again. I did this for about 15 minutes after which I prepared myself to finally take the photo. I raised the camera once more, but this time with the intention to take the shot. As soon as I released the shutter, one person screamed some incomprehensible sentence, which was followed by a large number of people all screaming as well and pointing their fingers at me. I was horrified and raised my hands up apologizing and slowly backed away. I subsequently continued my visit of the market, only taking pictures after asking for permission from my subjects until I was accosted by a gun-wearing uniformed individual who requested that I follow him to his office. After an initial cold and suspicious reception, a request to see my passport, which he inspect judiciously for what seemed like an hour, I explained to him what I was doing with my camera, and he became much more friendly. We ended up chatting for over an hour about photography, his military past, and life in Ghana and in the Unites States.

Switzerland

My home country. I was born and raised there and left when I was 18 years old. I found people there relatively easy to photograph although I found it difficult to find interesting characters. My experience there in photographic terms was much more subtle.

Greece

Second most difficult place after West Africa. I visited the city of Thessaloniki and stayed for about one week. People were very aware of my camera and often had a negative reaction before I even attempted to take a shot. Requests were often met with disgust and a negative response or with a demand for money. I absolutely love Greece and its people and want to go again to not only visit my DeviantArt friends but also to sample people's reaction to street in other places.

Colombia

A fantastic country, which I was visiting when writing this piece. Colombians are proud people and if they perceive your photographic endeavors as complimentary, then they will indulge. Candid shots are possible and often are met with surprise, in a way that makes me think of New Yorkers. My experience in this country is very limited and is unlikely to be representative of the entire country. I have only spent time in Bogota and Cartagena, a touristic city to the north of the country.

Denver

Denver lacks busy streets like the ones in New York or Chicago, but overall, people's reactions there are akin that of other major American cities: Surprise, curiosity, and once in a while offense.

There you have it! In closing, I would like to encourage all of you to continue shooting. If street is what you want to do, then great! If it's not, try different genres. And remember that practice makes perfect!