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Easy Mode:
The 'X' Museum of Local 'Y'
Plenty of boring cities have museums for just about anything 'first' in town. Water purification systems? Check. Railroad museums? Check. Nature museum with stuffed animals? Free wildlife practice check. These are either very cheap or free to get into and can provide with many kino as well as timeless shots.
Your Local Skatepark - Nobody has ever said no to me, all chads and dudebros want instagram fuel. 8+fps preferred. No butt shots. Only keep shots of tricks they actually landed (they get really butthurt and remember all the tricks they made that day, something that looks cool in the air to a normie will look dumb to anyone that skates and knows the person didn't land that jump). Don't ask for money.
Easy but pointless mode:
Local fair cover bands - will let you get up close and shoot them for free, will not contact you back though unless you're ultra good which you're not
The Sony Miami Experience:
Paid events with expensive sponsors that rich people like to hang out in. Stylish clothing competitions. Events that are catered by downtown coffee shops and clothing brands. Certain charity events. Cover price may vary, but you will be stepping in a land of very well dresssed people that you can snipe out as if they're there just for you. Optional achievement: Cloak and Dagger - Pretend to be the event photographer until the real one shows up. Cons: You might see them again at other events and can never go incognito again.
Medium Difficulty:
The Karate Kid feat. Gearwhorus
Got a fast bokeh Zeiss prime? Punch in martial arts places into google maps and call them asking for a free photo shoot for the business. Although everyone has iPhones today some moms will die for free BOKEH pics of their kids doing sports stuff. First one will be hard but on the second one you can show the pics from the first one and they'll go with it easier because iPhones can't into 80mil bokeh. Requires bokeh and high fps.