Ok, so it looks like the only way I will get the Print Organizer to work for me is if I can take an entire folder of cad + raster files & make each file have the raster attached before activating the print set. This is ok because I have the auto raster attach macro to attach the raster to the dgn when I open the files, but that means I have to open each one individually. I have created a .bat file that opens the correct version of Microstation + descartes but I don't know how to make it open a dgn & then close it & then move to the next file & repeat. This would solve all my issues.
Any advice?