This morning I stopped in at the body shop and showed them what I had done on my bumper. I asked them if they thought they could make it a lot better and they said probably a little but they would have to repaint a large area.. I opted to work with it a little more myself and call it good.
The worst part is the line behind the license plate where I had masking tape... (under the "S" in "State"...) No real good way to blend it in. Also the area where the mag drill was "mounted" is still pitted slightly but this is as good as its gonna get.
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We'll keep it just between us here...

Me thinks nobody will see it if you don't point it out.