For me it breaks when people try to make scripts/tools that are doing too much. Because at some point these break for variety of reasons.
Then wrapping my head around monster script is additional work I need to do on top of understanding system that is changed.
I argue that it might be quicker to understand system on its own and make changes manually than rely on someone else script.
In the end if script works it works time money saved - when it breaks it is more work and now there are 2 things one has to figure out.
That is why I'd rather have smaller scripts that do parts of bigger job instead of someone dropping "just run this and it will do everything for you" type of scripts.