Yeah, chkdsk from the prompt and by "scheduling" all it's really doing is making an entry in the Windows startup files. Whenever you then reboot the server chkdsk will run just before loading Windows and once done boot into Windows, no intervention needed from the point you click restart. Well, you could also write a batch script with "shutdown -r -f -t 0" and schedule a task to run that later in the night but maybe it's better you manually kick off the restart and then check back after say 40 minutes