Street shooting makes you learn your equipment
One thing I have noticed in my limited street shooting, just not much time to do it, is that it takes me a while to get over my shyness and to feel comfortable handling the camera in a new situation. These days, however, people are generally much more used to having cameras pointed at them and pretty much everything being recorded all the time. so, now, I feel people are less concerned about being photographed while in a public situation, so this may help some of us get over that initial shyness.
I also find, that when I am out, even in SFO, while visiting my daughter, people wanted to pose, and when handled in a frinedly manner it can be fun to meet people. I shoot with a Bessa R RF, and that is usually enough that people ask about it.
And, with the desire th have everything preset, I feel much more comfortable with my camera every time I get finished.