William Watson Goodwin, Syntax of the Moods and Tenses of the Greek Verb

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[*] 249. From the primitive use of the past tenses of the indicative to express what was likely to occur under past circumstances, we may explain the iterative use of these tenses with ἄν (162), which is generally thought to have no connection with the potential indicative with ἄν. Thus ἦλθεν ἄν, meaning originally he would have gone (under some past circumstances), might easily come to have a frequentative sense, he would have gone (under all circumstances or whenever occasion offered), and hence to mean he used to go. See SOPH. Ph. 443, ὃς οὐκ ἂν εἵλετ᾽ εἰσάπαξ εἰπεῖν, ὅπου μηδεὶς ἐῴη, (Thersites) who used never to be content to speak but once when all forbade him (lit. when nobody permitted him). Originally οὐκ ἂν εἵλετο would mean he would not have been content (under any circumstances), hence he was never content. The optative ἐῴη (532) shows the nature of the expression here. See the examples under 162, and the last example under 244.

This construction is not Homeric; but it is found in Herodotus and is common in Attic Greek. There is no difficulty in understanding it as an offshoot of the potential indicative, when it is seen that the latter did not involve originally any denial of its own action.