I like most people who have been around long enough, assess everything I do when carring out a ' risky' task. Eg- when cutting down or pruning trees. I look at the "what if's" as in what can happen if I do this or that , or how windy is it, will the best option be to use wedges. I used to cut and sell fire wood back in the nineties for extra income so I know my way around chainsaws.
My step son bought a house up the road that has been a rental for 19 years, the back yard was heavily over grown with trees. I cut a lot down, pruned a few and left a couple because they are too risky in their position for me to drop. I said to him to get a professional lopper in for those couple.