I mean "just" have a drone with appropriate sensors fly the length of the lines, looking for tree branches that are threatening. Perhaps using machine vision, or something simpler like lidar/radar/ultrasonics/whatever. Signal human inspectors when something looks fishy enough, with video attached for quick review/triage.
Optimally designed to allow recharging the drone's batteries somehow from the top of the pylons (aren't there electrical fields that might be used somehow[1]?), to allow extended automated runs.
Obviously covered in rubber or something to make the chance of damaging the infrastructure in case of a crash minimal.
Crazy?
[1] No idea if this is possible but it would be super neat since it might allow it to scale to run on hundreds of miles of power lines without many humans and with good coverage.