"Who gets the lawsuit when the falling gas can hits Grandma in the head? "
Oh come ON. What did you think I meant to drop a Gas can from 50 feet and let it splat!!!
No...You put it on a hook with a rope and slowly let it to the ground. Person on ground grabs container and releases hook. Vala!!! Some times a little common sense goes a long ways.
Better yet. Have a helicopter set up with a fuels tank in its cargo bay. have a Gas hose with a Nozzle that reels out to the ground below. You can meter it at 1 Gallon or 5 Gallons or whatever you want. Person on the ground inserts hose in to fuel tank and pulls trigger to fill just like he was at a prepay sevice station. You could even have the lower section of hose hooked via a self sealing quick connect that would release with say 20 pounds of preasure in the event that the helicopter were to get caught in a strong wind and pull intensly on the hose. This would be a safety measure. Where there is a will there is a way.