They do have chainsaws with automatic oilers but I think a chainsaw is the wrong tool for what you are looking to do for those heights. Chainsaws are finicky about positioning when cutting. The people who trim high lines and right of ways use a boom with a circular saw blade type cutting tool at the end.

Its also reatractable. I can't imagine driving around with a 40' pole sticking out from your loader.

Its also reatractable. I can't imagine driving around with a 40' pole sticking out from your loader.