The "Delay" action pauses rule execution and schedules a resumption, starting at the next action, at the specified time (5 minutes in your case) in the future. A "Cancel Delayed Actions" will, if run, un-schedule this resumption (which means that any actions after the delay will also not get run). This is different from a delay on an action (where delays on an action just schedule that particular action for the future and continue immediately on with the next action), but I see you already understand that distinction.
It sounds like you want some sort of repeated check. That won't happen here. After 5 minutes, your rule actions will turn off "DH Check Door Deck" and then immediately check if "KN Door Deck" is open and turn on "HD Check Door Deck" if so. If not, it will not turn on that switch. In either case, the rule is completely done at that point and will not run again until some event happens that matches one of your triggers (which, if this wasn't already apparent, is what will cause your rule actions to begin running, starting from the top).
This doesn't seem like what you want. It sounds like you want some sort of loop to periodically check, which is possible (RM has "Repeat" that can create looping blocks of actions), but it's usually a bad idea to do time-based checks when you could instead just respond to the event that made the condition you're looking for possible. If you explain the automation you're hoping to achieve (in real-world terms, ignoring implemantation details that may be RM-specific), someone might suggest a rule (or possibly another built-in app if you aren't set on RM) that could do this.
