You should try the check_mk´agent and see what already is possible! Log messages can be monitored and even windows services pr processes. You can define seperate service names or make a rule for example: every service with the setting automatic start should be running (but on most windows systems this isn’t the case).
But keep in mind that cmk per default get these informations one time every minute. When the server suddenly completely crashes check_mk only notice that the server is offline or when the cmk agent service isn’t running you don’t get informations.
Maybe additionally some active checks are helpful (check TCP connection etc)