I actually found a guy who does drone camera/video work that has hung 60ft XMAS tree light strings on tall trees. This might just work!
The antenna is a MyAntennas 130ft end fed that will run from my attic window up and over the tall tree tops behind my house. There’s clear space to run that wire from the window to the street in front of my house, so the end can be lifted on a little clamp and flown up and over the trees, to pull loose. I’ll add a 10ft line with 1oz weight to the end, so it will drop through the branches and hopefully given and take as the winds jostle the trees.