I was seeing the same error: "An item with the same key has already been added."
I found the issue appeared to be a presentation file for a subassembly in the drawing which referenced a historical revision of the subassembly that had since been revised i.e.:
(Assume everything was at Rev00 and is moving to Rev01, this is the structure of the drawing)
Assembly.dwg Rev01
-Assembly.iam Rev01
-Assembly.ipn Rev01
-subassembly.ipn Rev00
--subassembly.iam Rev00
-subassembly.iam Rev01
I had not revised the subassembly.ipn to Rev01 so I believe it would still have been referencing subassembly.iam Rev00, while the Drawing itself was referencing subassembly.iam Rev01
I have not replicated the error, but when I revised the subassembly.ipn and checked it back it to Vault, I was able to create the .pdf without an error