I can assure you that if the FAA allows 300/1 from Wall to JFK, then it will be over a very specific route, with obstacle-clearance taken into account. That's the way it's been since the days of New York Airways, and there is no reason to think it will change now. But I agree that if I lived in one of the numerous hi-rise apartment buildings between Manhattan and JFK, having a warbling S-76 come screaming over my head at 300 feet on a bad-weather day would not give me a warm&fuzzy.