Do Siri and Cortana escape the child's right to privacy?
Microsoft will not allow a person under 13 years old to use Cortana.
... should be flown a sufficient distance from populated areas
Am I to understand that you don't consider midtown Manhattan a "populated area"?
In theory, all aircraft (except toys, of course) are required to have an airworthiness certificate, as per FAR 91.203.
This vehicle would be considered a toy. The operators were certainly using it as a toy.
All life evolves by the differential survival of replicating entities. -- Dawkins