Why should a system be aware of anything? No need to bring consciousness into it. Entropy as a statistical concept was defined in post #2, and this logic should lead you to why entropy tends to increase- if you put a system in a low entropy state then there are only a few microstates corresponding to whatever macrostate you have. But atoms in a gas or solid are always interacting, colliding and transferring energy to each other. This happens so much that over some time, the entropy will increase to the point where there are many microstates corresponding to whatever macrostate you have.
It's a purely statistical result, if you start with 100 bottles of beer on the wall and then leave them in a storm, after a while you're going to have much less than 100. The macrostate of "all bottles still on the wall" corresponds to a single microstate "bottle 1 on the wall, bottle 2 on the wall... bottle 100 on the wall", and your system entropy is kb*log(1) = 0.
After 50 have blown off, your new macrostate "50 bottles left on the wall" corresponds to quite a lot of microstates. Bottles 1 through 50 may have fallen off. Bottles 1 through 49, plus bottle 51 may have fallen off. My maths is awful but I'd briefly guess that "100 choose 50" is the number of microstates of this new macrostate, so your new entropy is 66*k_B.
Obviously this example is pretty awful because there is a clear tendency for bottles to fall rather than get picked back up and replaced. But in a system of gas particles, or a set of paramagnets or all the standard examples, there is no macroscopic object (like the wind) forcing the bottles off the wall- just microscopic interactions which are completely random. And yet the system's macrostate will drift towards one with more and more corresponding microstates, so that entropy increases.
The more I think about it, the worse that example was