I cut trees for several years and still do on occasion for firewood or if a neighbor needs help. I just dropped two maples that were in an area just over 3ft wide between our property fence and the neighbors garage. Fortunately they were only just under 2ft in diameter but were close to 35ft tall each. That was a bit worrisome since his garage roof could have been easily destroyed if the trees fell and rode along the gutters. They both went down perfectly though. I figured my cuts for if the wind caught them or it split weird that the fence section would get crushed instead of his roof LOL. I use wedges also, really helps with keeping the tree falling where you want. I did have to block and tackle two beam branches that were overhanging his roof though. My son Jake stood on his roof to direct them away when I cut them off. Sometimes I have had to use a pickup truck to help guide a tree down in bad spots with 1" braided rope
It's a good job but not particularly difficult since a Doug Fir is pretty symmetrical and straight, not very lopsided with low beam branches and rarely have an odd lean. I also bet there was no wind! Try that with an oak, maple or elm and the approach would be quite different LOL. It would have had to be sectioned
In the backyard, I had a huge tree that has a bad lean so we cut 50+ ft off the top and now have a 12' main trunk banzai tree. Our neighbors think it's pretty cool. I prune it every Fall of anything overlong or heavy. It has one main beam branch that the swing hangs off of