Sorry, I want to make a comment that's not related to the substance of your post.
You seem to use the word "entropy" to mean "bad things", especially in the paragraph about "fighting one sort of entropy" etc. Using technical terms as metaphors is uncomfortably close to woo. So is the meme that "life exists on the border between order and randomness", which as far as I can tell arose from poor science reporting on the subject of self-organized criticality.
To clarify the difference: this is woo, and this isn't.
ETA: Turns out Shalizi has a note about the above-mentioned meme. (If someone is unfamiliar with Shalizi's notebooks, run don't walk and read as many of them as you can.)
I may not have my idea of entropy clear enough, but when I say that totalitarianism is lower entropy than authoritarianism, I'm not implying that entropy is equivalent to "bad things". What I've got in mind is the idea that entropy is what happens unless an effort is made to get something else to happen.
I suggest that there are default patterns for social groups, and they could be viewed as high entropy-- what you'd expect without knowing more than that there was a social group of a certain size, possibly with some modifications for tech level and status.
For example, I think that authoritarianism is the default for government-- "we're in charge because we're in charge, and it would be dangerous for anyone who tries to change that". Totalitarianism is lower entropy-- it's surprising for the people in charge to have an ideology which requires them to make drastic changes.
The recent Elitist Jerks: A Well-kept Garden describes an effort to fight one sort of entropy (the repetition of the same questions and answers) which resulted in another sort of entropy (an excessively stable and eventually fragile core group).
Maintaining fun is another challenge in the keeping things alive category. Pleasant is relatively easy. Fun (which I'd say requires novelty) is harder, and I'm interested in comments on what it takes to keep the fun going.
There's a theory that life exists as chaos on the border between order and randomness-- I find this plausible, and it's a different angle for looking at the Friendliness problem. How can a system be built which continues to permit (or even encourage) interesting sorts of change, without permitting change so drastic that we as we are now wouldn't recognize the outcome as still related to us?