Thanks for posting the description of the bumper tips. Your picture from the bottom of the compound bend and your description made it all click. I made a tip out of 1/8" flat stock and thinking of welding 6 inches of that tip onto thicker flat stock or channel and hiding the seam under the diamond plate. The compound bend not only made the bottom curve In, but it also curved the whole edge. I put the flat stock in a vise and tightened it at one and pushed until 45 degrees in the picture , lowered it to two and pulled it 45 degrees, then lowered it to three pushed it as needed. I also think I got a good measurement. The bumper is flush with the bottom of the fender and everything looks good so far.
I might need to cut more than 2 3/4 off the diamond plate to get rid of the distortion from the rust, but I don't think that should be a problem.
Thanks again murphy98