I suppose the prevalence of psychological "disorders" diagnosed on the basis of "distress" might be such a benchmark. How many "maladapted" "malcontents" or "misfits" does the society create?

Not so long ago, when Western culture was a lot more misogynistic than it is today, women would be diagnosed with "Female hysteria", and one of the symptoms was

... "a tendency to cause trouble".

...

A physician in 1859 claimed that a quarter of all women suffered from hysteria. One physician cataloged 75 pages of possible symptoms of hysteria and called the list incomplete;^[2] almost any ailment could fit the diagnosis. Physicians thought that the stresses associated with modern life caused civilized women to be both more susceptible to nervous disorders and to develop faulty reproductive tracts.^[3] In America, such disorders in women reaffirmed that the United States was on par with Europe; one American physician expressed pleasure that the country was "catching up" to Europe in the prevalence of hysteria.^[2]

(my emphasis)

Was the 1960's counterculture, evidence of systemic cultural dysfunction?

Keynesianism is intellectually hard, as evidenced by the inability of many trained economists to get it - Paul Krugman