This maple is about 90' from my house and over 100' tall. Most of the serve weather comes out of the SW and would likely push it straight back so not a major concern. I want to preemptively drop it to the left which clears any snags. I am decent about putting a straight tree anywhere I want it to go; however, how do you deal with a hollow/rotten trunk that doesn't permit for a basic felling cut and wedge use? Afraid the slightest cut and things could go wonky. Hollow/rotten at least 7-8' high.
I'd cut a very shallow notch down in the root flare where there is good wood. Then bore cut the sides and leave a back strap to release it. id probably have a rope in it toward the direction you want it to go and pull it over with a come along.
Look up cutting or "felling" a catface tree. Should give a few ideas and things to think about. A catface is never fun and each is unique to itself and general advice should be taken with a big grain of salt. Owl
Consider a scaffold or something. Cut it high over the hollow section and then take the shortened stump down with a bucket pushing it at the top the direction you want.