In trying to come to terms with this hyphen-thing, I have tentatively concluded that hyphens are more akin to letters rather than to words. As I see it then, hyphens (and other elements of punctuation) seem to be part the mechanical underpinning, or infrastructure of the written word.
Thinking with this tentative conclusion, the idea of prescriptivism vs. descriptivism does not seem to neatly apply to the rules governing the use of the various hyphens.
I tried an analogy: What if an author persisted in using an “N” where an “M” was required, or a “V” where a “U” was required? Or other arbitrary, near-look-alike letter substitutes? That little squiggle on the “Q”, for instance; what would be lost if an “O” were substituted?
I might consider the author to be functionally illiterate. But only if I knew the letters well enough to notice the deviation from standard practice.