Yes, I have thought about this and discussed it with a couple of my friends, none of whom own a drone.
I have a tree that is about 10 feet from the property line that I would like to use as one anchor point for one end of a wire antenna. There are two problems with this:
1) there is another tree between it and open space
2) If I stay on my property, the angle is too steep to shoot an arrow over the desired tree without having it come down in the second tree at which point I can't recover the line or the arrow. I have never really gotten along with my neighbor. Common courtesy dictates that I am not going to go on her property to shoot the arrow and I am also not going to go over and ask her permission. Again, if I stay on my property I am shooting the arrow at maybe an 80 degree angle and it comes down too close to the tree to recover the arrow. I need to stand back a lot further (on her property) to pull it off.
So I have spent a lot of time thinking of a way to get a line over that tree. And, at one point I thought about tying a fishing line on a drone, flying it over the tree and then landing the drone on the other side. Walk over, get the end of the fishing line, then tie a bigger line onto the fishing line and pull it back over.
The only thing stopping me is that I don't have a drone to do it with.
A few years ago, I had a tree get hit by lightning and it split the tree from top to bottom. This tree was about 80 feet tall. I was afraid to cut it down myself because if anything went sideways, it would fall on my neighbors garage and boat. So I hired a tree trimmer to take it down. While he was here, I asked him to use his bucket truck to put a line over another tree of similar height: the tree trimmer estimated it to be over 70 feet tall. I took some antenna rope, tied a 12" wrench on the end and told the guy to go up in the bucket and simply toss it over the tree. It fell to the ground with the weight of the wrench and I hoisted up one end of the antenna. I then asked him to do the same at the other end with the aforementioned tree and he said the ground was too soft to drive his truck over to the other tree but if I called him back, he would do it when the weather was drier. However, I have called him back and he never got back to me: I don't think he wants to come out here to do that even though I would be happy to pay him whatever his rate is for a very simple job.
This brings us to plan C. If I can't do it any other way I am going to hire him to take down another tree (the one my antenna is in now) and while he is there, have him put the line up over the tree I want to use.
This tree is a little taller than the one my antenna is in now, but the big thing is that if I can get the antenna in that tree, the feedline will fall directly down to my shack window. As it is now, it falls about 10 feet to the side (right over the driveway). So its a win-win: the antenna will be a little higher and the feedline will be perfectly positioned. As it is right now, my antenna is about 70 feet high on the ends but the center sags down to about 35'. I have a fiberglass mast outside my shack window with my 2m/440 antenna on the top of it. If I get the antenna in that other tree, and the feedline falls straight down to my shack, I can then use the fiberglass mast to support the center of the wire without causing the fiberglass pole to bend over. I am hoping that the wire antenna will sort of guy the fiberglass pole and allow me to extend it all the way up (50 feet).