Here's a real silly question...what type of garage door do you have? You have a "Garage door opener" changed...this isn't a MyQ unit where you have an opener, a closer and then the door, correct? If not, then it would be more accurate to have "garage door" instead of garage door opener, since the door can be open or closed. less confusion that way.
Have you confirmed that when the door is closed the device reads as "closed"? Can you also show a screenshot of the door opener edit device page?
Your real issue is that your first delay, the 30 min one, doesn't have a cancel on it. So, you aren't even in the repeat when the cancel actions is occurring....and then when it gets there, it can't cancel them again, so you're stuck. And the cancel to the first delay and you should be all set.