I'm chalking this one up to gremlins and since I now have a solution I'm good. Here's the code that I added to the Word template that I assume caused the issue in case anyone is interested. Restoring a previous version of the template that does not have this code resolved my issue.
Till next timeDim InAcRsn As String '''''Manages "Inactive_Reason" dropdown. With ActiveDocument.FormFields("Inactive_Reason").DropDown.ListEntries .Clear .Add " " .Add "Deceased" … End With If InAcRsn = "" Then ActiveDocument.FormFields("Inactive_Reason").Result = " " Else ActiveDocument.FormFields("Inactive_Reason").Result = InAcRsn End If