I'm studying for my drone pilot license; this is in such a grey area right now it's probably going to take a supreme court case to iron out the legality. First there's the issue of private landowner's domain, which has already been decided in the Supreme court as everything ground level up to at least 365 feet above the ground. Drone's are only legally able to fly below 500 ft, which allows 145ft of vertical air space this drone will be allowed to fly, except over the tallest structure in an urban area, where the drone is allowed to fly 360 ft above the tallest point.
Seeing that the pilot can ensure that he is flying at the correct altitudes, he also has to make sure there is no-one below his flight path that isn't directly involved, or made aware of the flight. Clearly, he didn't do this. The next part is Orlando requires drone pilots to know acquire permits under certain conditions:
Rules he may have broken here are being within 500ft of that school/the theme parks population (although that may be more than 500ft).
The problem with this Orlando ordinance is the United States Government has exclusive sovereignty of all airspace in the United States. This means that federal law in regards to air space will always trump local ordinances. Therefore, since none of these local rules are federal law, they aren't enforceable in a Federal court. Basically, a pilot could get fined by the city of Orlando for breaking their ordinance, but all the pilot has to do is go to a federal court, pay all court fees to challenge the city of Orlando and the fine will be dropped. Problem is it just gets more expensive to fight the fine than pay it.
Personally, I wouldn't want to risk losing my drone pilot license so I would just stay away unless I acquired a permit from the City of Orlando.