I kept logbooks throughout my machining career - one with the day to day stuff (like a diary), and one with all the technical stuff - tool numbers, tooling lists, setup notes, program number, etc. Even a decade after I've retired they are both interesting reading, and excellent references if need be.

I thank an old timer who set me on that path in the first weeks of my employment in the first machine shop i ever worked at (way back in the Stone Age). So what I am saying us - get in the habit of writing it down and organizing it as a document. It trains your mind to consider the whole project from end to end.

The stuff to really figure out is what you can pull off on corners, inside and outside. On wood, it's what you can pull off on an outside corner which is trying to split the grain- that's going to be your limiting point every time. For finishing passes, you can keep example pieces.

With the what I am using I can save a MOP into a file and load it later on a different model and just select new geometry and boundry

Is that in VisualMill? I didn't know you could do that.

How did you handle the revisions? That's what trips me up. I'm currently re-drawing every part on every model we make and there are thousands of files to sort through, delete or archive.

VisualMill has a feature called knowledge base where you can save off entire machining strategies. I use this a lot and it comes in very handy.