Yes. First add your documents in the Sales Coach / Resources page. You can create new documents or upload existing ones.
Then go to Settings / Custom Deal Fields. Select the Product field (or add it if necessary) and then add the list of options, eg Product A, Product B, etc. For each one you can select a document.
Now when you edit any deal (go to the Prospect View and click on the deal name to edit) and select the Product(s) relevant to that deal, the associated documents will be shown in the Resources tab in the Sales Coach display.
In a similar way you can add a comparison type document relating to each competitor option in the competitor custom field. When competitor X is selected for a particular deal, the Competitor X comparison document is displayed in the Resources tab.