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Hi Andrew-
I imagine there are a number of ways to do this, but here's one: We are using WF4 and WC 9.1. If you open a drawing, do a'save a copy'and choose *.pdf, there is an option to 'save new file to model's CAD document.' Once this is done, the pdf of your drawing appears on the info page of the CAD document under General-->attachments. I believe this method also throws up a flag when the secondary content (in this case the pdf) is out of date. One caveat of this method is that Pro/E currently will only (as far as I know) save to an A-size pdf.
-Randy