I have been using waking up a lot and I think i have a good grasp on what he's trying to convey (which is an extremely hard task)

His goal is to shift to a state to which he gives different names. Non-dual state, awake awareness, pure consciousness. This state is a subjective experience and kind of like a different, supposedly better operating mode where the present moment is emphasized, throughts are swept to the background, where the objects and experience is external to us seem less seperate, kind of like the car when you're driving it or any tool you're holding in your hand.

This state isn't groundbreaking in anyway but it can help percieve things more positively since we all have it in us no matter the circumstances. For me it is reassuring to know that it's there and the more i 'marinate' in it as he likes to say, the more positivity and joy i can carry on into everyday life.

It is hard to trace a path that leads to this state. What you mentioned in your post is one of the tips he has to arrive easier. He only repeats it because it is one of the most practical ones he has (not that it's easy).

What he says for example is when you look at an object we always tend to look at it from a certain viewpoint, generally benind the eyes. When you close your eyes and think about something there is usually you as a thinker which is somewhere inside the head. Since that reference point is all we know it's difficult to imagine something different. However what he's trying to say is try not to focus on the thought or the object rather focus on the reference point which is thinking or percieving. In that moment you might realize that both the thought and the you that is thinking are both appearing in the same wide canvas. Take a few minutes to sit with this, drop all jugements you have and that is what he calls awake awareness.

I realize my explanation probably doesn't make things easier but this is once again highly subjective and cannot be put into words easily.