Ryan, you sound like my old man
A few years before he retired he would always complain about all these new young guns they would bring in where he worked
Young kids would all get tasked with a job to fix, design build something and the young kids would have all these drawings and numbers ect... and bring them to my dad to fab up stuff.
My dad is a man with no education and 50yrs experience making just about anything you can think of would look at the drawings like
Question the young new workers about measurements written down for cutting and truing things to specs what were no where near achievable with the tools/equipment the place had
on top of simple design flaws
He would say, this isn't going to work, make it, doesn't work, young guns all confused then the kids would tell him some rough dimensions of what they needed and he would just make it like he had done it 100 times.
basically when you get experience working with tools/materials you learn what is possible and what actually works vs what is theoretically possible.
Similar things can be said for skilled wood workers. Ask a skilled wood worker to make you something out of a random type of wood and they will have 100 reasons why not to use that kind of wood and why to use this other type, they just know.