Please help! Assistance needed

Hello, I am trying to fine something for a friend of mine.

Problem: There is a 145 page PDF/Word document that contains numerous inspection points. An inspector goes to a building and marks the sections in which they failed. For example, a building xxx failed A)14, A)18, A)110, etc. That document then needs to be translated into a new PDF and only contain the sections in which the building failed inspections. This is currently done manually by copying and pasting and consumes a large portion of the day.

Is there any easier way to somehow have a program,code,app, anything that can is able to have the user select sections from a PDF/Word document and populate in a PDF/Word document.

I’m racking my brain on this and seem to be stuck. Any assistance would be greatly appreciated.