"The entropy of the probability distribution describing the system" only has meaning if there is an observer to actually hold that probability distribution. Since probability is in the mind, there is no fixed external thing that just "is" the probability distribution of the system.
There are two distinct things; one is "the system" and the other is "the probability distribution over states of the system." If you make an idealization and do math just on "the system" then the distributions in those idealizations are entropy increasing (if you exclude any observer or external stuff to the system). That does not correspond to reality (because the system's not truly closed), but is often a useful approximation for describing "the arrow of time."
If you want to talk about "the probability distribution over states of the system" then you must also be including some observer with a mind of some sort, or else the notion of there being a probability distribution (as opposed to just whatever the deterministic eventuality of whatever does in fact occur) doesn't make semantic sense.
So, to speak about the "probability distribution of the system" there has to be a Maxwell's demon sitting there having that distribution in its mind (e.g. some observer), and whatever entity it is that is dissipating waste heat while doing physical processes to update its beliefs must be increasing entropy.


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I appreciate your patience with me and for the help in getting me to confront my confusions about the topic. Your answer still is unsatisfying to me, and this could totally be my own ignorance at work. However, I cannot understand how your answer is sustainable given the comments at both the Stack Exchange post and at the John Baez link.
I think you've misunderstood me when you articulated the 3 positions listed above, but you've definitely hit upon my confusion so I need to think about it more carefully and do a better job saying what I want to say. I will think on it and write again when I get a chance this weekend.
Again, I do appreciate the patience in helping me understand it.