Entropy may always be increasing in the universe, but I would argue that so is something else, which is not well-understood scientifically but may be called complexity, life or intelligence. Intelligence seems to be the one "force" capable of overcoming entropy, and since it's growing exponentially I conclude that it will overwhelm entropy and produce something quite different in our region of spacetime in short order -- i.e. a "singularity". If, as I believe, we are a transitional species and a means to a universal singularity, why would I want a system which restricts changes to those which are comprehensible or related to us?
Intelligence has discovered nuclear fission - and is working on nuclear fusion. It looks set to be the greatest entropy-creator evolution has ever invented.
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?