Everyone in NYC has that one bodega where the cashier makes up prices when you're checking out, and it's sort of a sign to avoid them when they overcharge. Sounds like you're just making very poor buying decisions almost regularly, and expect the same results as if you were making good buying decisions.

Try doing the following:

• Buy food, beer, coffee, and snacks at a grocery store.
• Prepare your own food/coffee instead of ordering takeout & delivery
• Always have cash on hand to avoid the convienace fee, or forced overtipping
• Withdrawing a set amount of cash over a set time period also helps you to budget your small purchases