I have not been able to figure this out, but given the number of people who create PDF's of their released files, I would think that this has to be feasible.

1) When transitioning a file from review to released, there is an action / task that auto generates the pdf.

2) The problem is that the PDF file comes in as being "in design" as that is the initial state of the workflow.  It should be released, same as the slddrw......as releasing it is what generated the pdf in the first place

The next issue then becomes putting the drawing on hold.  I have added pdf as a drawing node, so that when you state change the SLDDRW to on hold, you have the OPTION to change state on the pdf as well.  Ideally I want that to not be an option that someone could forget.......wherever the SLDDRW goes in the workflow, so does the PDF.  No questions, no thoughts, it just follows.

Are these 2 things feasible?  Thank you in advance