Always on except...

Hello everyone, first message here and brand new to GHL/automation, I know very little. A few questions, is it possible/how would I do this?

1. Set a powerbar socket to be always on except for if power is drawn during a certain time and receive a notification that the power was cut. Reason is this, light has a timer (ATI sunpower dim), if lights timer fails I want to know. If i simply told the power bar to cut power at the same schedule I would not be alerted the lights timer failed, right?

2. Is it possible for the GHL to detect a powerbar outlet failure on it's own? Can it see that "outlet 1 of powerbar should be drawing power but is not" and notify me?