I've been dealing with this issue for some time.
I have a plan with multiple hatches, set with various transparencies.
If I create a PDF (using DWG to PDF.pc3) with 'plot transparency' checked, the PDF looks fine, but when if I send the PDF to the actual plotter, Adobe crashes or part of the PDF will print.
If I uncheck the 'plot transparency' and create a PDF, this PDF will print to the plotter without issue (except the hatch all looks terrible).
Is anyone else dealing with this issue or able to plot large maps with several objects using transparencies?
Any help would be greatly appreciated.