This called for a drone. Mr. Riddle went on Amazon and bought an Ionic 6-Axis Quadcopter Drone with a camera for $69.99. He flew it in his apartment. He said he looked up laws for using drones on Google and, satisfied he was out of the forbidden zone around airports, packed the drone in a duffel bag and took the train to Midtown Manhattan.

“It wasn’t the best idea,” Mr. Riddle said, “but I figured I had it in me.”

He saw some police officers standing near Macy’s and approached them. He told them he wanted to fly the drone straight up and let it descend. He said an officer replied, “Sounds O.K. to me.”

Thus feeling empowered with a municipal seal of approval, Mr. Riddle set the drone on the ground by 350 Fifth Avenue.

“Turn it on, start flying it up,” he said. In that moment, he unknowingly entered the extremely complicated legal realm regarding drone use in New York City, one that cannot be easily explained by Google and has led many an enthusiast to arrest. Steven Cohen, president of the Drone User Group Network, said last week, “The simple advice to anyone wanting to fly in New York City is: don’t.”

Mr. Riddle said his drone flew up to about the sixth story before the trouble began: “The wind takes it, and it bumps against the Empire State Building a few times.”

Not good.

“I let it drop, and it falls onto the first tier, which is like five floors up,” he said. He entered the lobby, approached a security guard and asked to get his drone back.

“You got some ID?” the guard said.

Later, while he waited, a police officer arrived and arrested him on charges of reckless endangerment. In an apparent misunderstanding, and a final indignity to Mr. Riddle, the police reported that the drone had flown up 40 stories before falling, a height Mr. Riddle had only dreamed of reaching.