Hi @loganross
Files properties is only avaliable in contact properties, not in deal, and i think workflow cannot import file.
Some ideas:
1) You can create one field text in Deals Properties, to paste in Workflow the URL of document online.
2) U can create one landing page simple, with form with FILE field, to your deal or sales team upload the file with informations you need, in this form/lp, and this doc will be added in contact properties. For this example, you can configure workflow to send one email for each deal with this landing page andwith the document to him download, reply questions, and upload in LP.
Hope this helps.
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Best regards!