Another update on my experiment. I haven't tried using vinegar on it yet. I think it is interesting the area on the bottom and sides, which were a darker color after using the SS brush/Drill, are now a lighter color. It's like the iron was changed by the crud and can't take the seasoning as well as the other areas.
This is why most folks don't use power tools on cast iron cookware. It does something to the surface and will never season the same. It's possible to intentionally rust the affected areas and get the surface back to something you can season. My theory is that the steel from the brush is actually transferring to the iron and creating a sort of "plating" or steel or stainless that won't season like iron.