[ghomem]

"configuring a Linux base image for a specific server role" doesn't have a single desired outcome. There are a million ways to accomplish it. No two sysadmins would produce the same result.

This is not right. There are a million ways to implement the process. Once the process is implemented there is a single desired outcome which is the correct configuration, and every other outcome is undesired - you can have a procedure to test the servers, confirming if the configuration is correct.

The "million ways to accomplish" define a million different processes with different entropy levels. The ones with lower entropy levels lead you to the desired outcome more often.

"And in the case where you're re-following the same process but with newer dependencies, "

If it brings newer dependencies when you re-follow it is not a good process. That is one of the points to have in mind.

"I just don't follow how this insight is meant to make it possible to evaluate how to get out of this mess?"

Entropy is a way to count the failure modes of a process. For a given business requirement chose the simplest possible that respects it. I gave two examples in the article.