Afaics, your conceptualization mistakes aliasing error as reality.

You take the point sample in spacetime of pouring a cup of coffee and presume that the microstates are ignored by yourself because they don't impact your perception of any event or state which is perceivable by you. But you are not factoring in the future of the Butterfly effect of those microstates' entanglement with the environment and the changes to the future you will perceive in the future based on the microstates in the cup of coffee you are pouring at the moment in time.

Thus your entire conceptualization collapses.  

Quantum mechanics models the microstates superimposed, because otherwise measuring the position at any point sample in time is aliasing error (a random result). Analogously we must model the entropy as superimposed into the future in our macro perspective. Your conceptualization of entropy as relative to an observer ignores the fact that the entire future is entangled with the entire past. Our perception of reality (decoherence) is but an aliasing error illusion. Information (order) is our mutual synchronization of a specific instance of illusion.

I hope you realize I'm stating that the objective reality is an unbounded superimposition of multiverses. Our perception of our universe is but an aliasing error illusion. And even humans don't share one consistent illusion (c.f. my prior post). The entropy of the universe is unbounded. Entropy w.r.t. to an observer is an ill-defined concept.

(P.S. I am still having significant issues with cognitive energy and its root concomitant gut/liver health. I am not able to explore this space we are discussing with the assimilation vigor that I feel I had been accustomed to. So do please understand if the limits of my current health prevent me from continuing the discussion or making the level of insights and explanations that I might be capable of at some other time.)