I would try to machine the top photo first. To do the second side I would use the bolt pattern in the big oval to mount it to a plate and them machine the second side. Same with the second piece. Do the bottom photo side first and again mount it to a plate. If the holes in the bosses are through holes for bolts drill under sized and tap them for mounting. After your done drill out the threads to the required size. I have done that a few times.