Renting from a stranger seems less risky, at least financially. But you don't know if the boat is seaworthy, maybe a small boat on a small lake would be an acceptable risk. I would stick to reputable rental companies.
Renting a boat to a stranger seems very risky. What if they crash the boat and drown? What if someone on the boat is injured or killed? What if they hurt someone else with the boat? No way I want that responsibility.
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