I have the same problem, and must deal with it soon so took the time now to prototype what I had in mind. It will work, I have been testing it manually, and the macro to drive it will be very small.

1. Set the watermarks in the master copy of the Word documents. Use a text box, not a watermark. For the company name, use a custom document property. Rotate, position format as required for the document.

2. The "Get it ready to send out" macro will be a small one.

a. show a file picker for me to choose the documents
b. prompt me for the company name and the destination folder for the PDF files
c. loop for each chosen word doc:

I. open it
II. update the custom document property value with the new co. name
III. update fields
IV. Maybe unlink the {DocProperty} fields but that is probably not necessary
IIII. save as PDF of the same name as the original Word doc
IV. close the Word doc without saving changes

Hope this helps,
jw