Mac,
While poking around Account Settings in Outlook, I realized that we've been using the free version of the Outlook App that comes pre-installed with Windows, instead of Outlook 365 that comes bundled with Office. I switched to the full version of Outlook, which did not have any issues printing (and did, in fact, create the Outlook directory in %AppData%\Microsoft).
Thanks very much for your willingness to help fix the issue!!