1) make anyone uncomfortable
2) shoot people and then laugh at them and tell them that you are entitled to shoot them if they are angry
3) make anyone upset
You'll be fine.
Most times, a lot of the people making noise about so-and-so being uncomfortable are not the people being photographed. Some are making noise out of genuine concern, others are making noise to feel like they have a moral higher ground. Learn to explain yourself (if you feel the need to) to the first group, learn to ignore the second as noise. I think being sensitive and streetsmart are skills that you have to develop by yourself. The two are separate.
One has to do with respecting your subject. Would you wnat to wave a photo around if the person you had shot was unhappy about it, despite all the laws in the world supporting you? I won't.
The other has to do with protecting yourself. Waving a good photo around would make no sense if you end up getting beaten up, getting detained, getting a black eye for it. Observance of body language, knowing how to react to people confronting you because you misjudged... Street photography is not just about taking photos, it is about blending in, observing people's behaviour, knowing how to get it without being intrusive.
And yes, I can't say I ever agreed with Bruce Gilden's style.