Having joined may father and his friend during the process of cutting down big trees in the village neighborhood I can personally vouch that this indeed a cumbersome and very complex task for both the planning and the execution phases. However, for us the tasks are made easier by the trimming of the tree's branches since my father's friend is the expert tree climber.

From your descriptions, it seems that your tree cutting procedures do not involved precut of the tree's branches before cutting the tree down.

I've got the feeling that this cutting tree problem can be solved by constraint programming techniques [1],[2]. Alternatively generic tools for constraint programming, for example OR-Tools and MiniZinc can probably do the same if not better [3],[4].

[1] Logic, Optimization, and Constraint Programming: A Fruitful Collaboration - John Hooker - CMU (2023) [video]:

https://www.youtube.com/live/TknN8fCQvRk

[2] "We Really Don't Know How to Compute!" - Gerald Sussman - MIT (2011) [video]:

https://youtube.com/watch?v=HB5TrK7A4pI

[3] Google OR-Tools:

https://developers.google.com/optimization

[4] MiniZinc:

https://www.minizinc.org/