The bold operation is the last operation created. It will have nothing to do with anything except as a reference. Not sure about why it's not showing in Mach2, but you could look at the code and see if it's doing what it's supposed to do. You've got 1 chain in each of the 2 ops, but 2 drill points in the single drilling ops. Are you drilling both parts at once? If so does it show up in Mach2 like that? If so, why not do the contours the same way? One operation with 2 chains.