Well first of all you don't need to login to apply updates, PC Monitor doesn't require any logging it, right?
Also I would never allow automatic updates on a production windows server machine. Mainly because of the unpredictable problems that may appear. In two years of my IT Administrator history I've lived to see Windows Server 2003 critical IIS update that 'forgot to start IIS back after the update' or a service pack for SQL Server 2012 that literally killed the application itself and I could go on with a few more.
Always apply all updates by hand and always triple check overall system functionality after an update restart. If you would like to automatically install windows updates why not enable automatic updates in windows? That will only install important updates.