If a city/municipality issues a permit to film a commercial activity and has PD on site to assist and the pilot deviates from what they tell us and violates FAA rules, what exposure does the city/municipality have to FAA fines?
Every incident is analyzed on a case-by-case basis. Generally, a city is liable to the extent that it authorizes the operation. Deviations outside of that authorization are generally not considered as violations by a city.
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