As a consultant touting how easy it is to use ArcGIS Online for self-service mapping and content management, many of my clients comment on how any "clicks" and windows it takes to get something as simple as a PDF up into the cloud. I would like to see added functionality put into the already existing AGOL connection manager icon in the taskbar to enable users drag and drop functionality directly to their private organizational workspace - with the ability to enable sharing across their organization.
This is a much simpler approach to navigating to AGOL, signing in, clicking into the personal workspace, select the Add file and browse to the file...