Even though I have stopped my skydiving when my son was born, I still dream about it and thinking how would it be good to jump out of the plane (with parachute) every time I fly somewhere.
I have ordered a Lily drone and thought it would be good to skydive with the drone. I did my search and found no evidence of such experience.
I assume there would be need in some adjustment in algorithm of the drone to compensate for unusual pattern of required stabilization, when there is a updraft, gyro “feels” the fallout and need to keep a tracking of falling object.
Theoretically this type of motion control requires less energy as it should compensate for difference in air resistance between skydiver and drone (which can vary based on type of exercise) and for stabilization.
Time of flight can be very short e.g. head down freeflying (~260 km/h /160 mph) or style, when speed of fall is more than 400 km/h / 250 mph. It also can be very long e.g. cross-country jumps.
It can be (mainly) vertical or (mainly) horizontal, like in wingsuit flying.
Another critical complication is safety. Not that it is not important on the ground, but in the air it can easily become a deadly move, especially during the parachute opening. To ensure safety the drone has to keep a minimal horizontal distance from the skydiver at any time of the fall and in case of horizontal component of the fall (usually there is some) to avoid being on the way. That keeps some limited area that drone has to stay within. E.g. in case of vertical free fall the drone can be within the green area and outside of red.
So I assume soon we shall see the amazing views… hard to believe, but even more spectacular than those.