Okay, so I didn’t go to the Academy, but I did Navel ROTC, which used some of the same leadership training materials.
And yep, something very similar to that flagpole thing really was a question.
As I recall, it wasn’t about flagpoles in our case but something equally filled with technical details we midshipmen could have spent an hour working out with our fledgling engineering math.
And of course the answer was, delegate to your chief, what do you think the Navy pays him for? Not only has he probably been doing this for more years than you’ve been shaving, but he can run a calculator just as well as you can and he actually knows where to go find the guys to use the paint brushes.