Phrases – Alternative Expressions for ‘Luckily, It Could Have Been Worse’

The phrase know which way the wind blows is quite old. Even the sense of "knowing the direction of public opinion" dates from at least the early nineteenth century (see The Phrase Finder).

There is a slight association between that phrase and a "weatherman" that dates from at least the early twentieth century. There was a classroom activity called "Weathervane" to teach compass directions in which one person was designated "weatherman" and called out an arbitrary "direction of the wind" (description).

Beyond those facts, there seems to be little evidence that Dylan's lyric existed as a phrase before he set it down in the Sixties. (It's hard to prove a negative, of course.)

It means ‘take revenge’, as in this quotation from William Thackeray in 1849: ‘You see if I don't pay you out after school—you sneak, you.’ It was still being used well into the twentieth century. It is appropriate in the work of the Rev. Awdry, but seems to be in decline, as this nGram shows (subject to the ususal cautions about nGrams).