There are some of us that are blessed with a keen eye, steady hands, and all the coordination in the world, and then there's the rest of us.
I've been using a Granberg version of your Oregon filing guide for a long time, after I loaned out my oregon one and never got it back. I wouldn't last long without it...my normal procedure is to file a chain with the jig, paying attention to returning all the cutters to exactly what I want for angles, and length, then I go out and hand file 2 or 3 times and get 'em all screwed up, so I have to re-file in the shop.
Clamp your bar in a heavy bench vise, then mount the guide...puts everything at a comfortable height. After a short time, you'll find that you can get a 16" chain done in about 10 minutes, and sharper than the kid does with the grinder at the hardware store