Reply To: Downloads/associated documents in the sidebar?
You could use the listdocs shortcode in the sidebar element of a task. However, like John, in my experience, users tend to view the right hand sidebar as “vaguely related” content that will take them elsewhere, and they tend to be blind to documents in the RH column. For documents that pertain to the task in hand, there is an “Attachments” panel where you can select documents to appear in a prominent box at the bottom of the task, which is more visually prominent than inline links to docs.
Hope that helps.