Drawfiling takes some time to learn and gain control. After this, it really is a great process that creates a remarkable finish without too much work at all. I often go from drawfiling straight to barrel finishing.
A few notes...
I like to use about an 8" file.
Check the file for straightness by sighting down it's length. Assuming it is straight is a bad approach. If it is bent, your best to put the convex side down.
Hold the file close to the barrel to maintain maximum control.
I think I show this whole process in a video that you can check out.
As far as barrels go, we side mill the flats so they are very flat. Cutters can wear a touch but the amount that the flats vary from being flat is very minute. Some manufacturers use a facemill to cut the flats. With a swamped or tapered barrel, this creates a very small hollow in the cut.
As you demonstrate, light can show deviation, but it is extremenly sensitive. A thousandths or two can look like a mile, so it's good to keep this in mind.
Jim