When in doubt, shoot it. You can always decide later if you like the photo or not and make edits in color, exposure, cropping, etc. One thing you have less control over in editing is the composition so do take time to properly compose your photo as you like. If you're shy about photographing people, you can always be discreet or just ask. Most people won't mind and are clued into the popularity of photography and visual expression so they get it. I can't not take photos just about anywhere I go, even at the grocery store. My biggest tip: just take time to appreciate the things right in front of you - that's the beauty of street photography - we're able to capture objects, art, design & architecture other people make, and people just doing what they do. More often than not, those candid moments make for the most compelling photographs.
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