ὑψίπολις seems best taken as =“ὑψηλὴν πόλιν ἔχων”: cp. Pind. P. 8. 22“ἁ δικαιόπολις...νᾶσος” (Aegina). In Pind. O. 2. 8Theron, tyrant of Acragas, is called “ὀρθόπολις” in an active sense, as=“ὀρθῶν τὴν πόλιν”. In O. T. 510 “ἁδύπολις ῀ ἁνδάνων τῇ πόλει”: but it is harder to suppose that “ὑψίπολις” could have been intended to mean, ‘standing high in his city.’ Nor would that be the fittest sense. The loyal citizen makes the prosperous city; and her prosperity is his. See on 189. In this clause the Chorus thinks especially of Creon (191 “τοιοῖσδ᾽ ἐγὼ νόμοισι τήνδ᾽ αὔξω πόλιν”).
ἄπολις. Where the typical citizen is a law-breaker, the city is ruined, and the evil-doer is left citiless. So Creon had described law-breaking as “ἄτην...ἀστοῖς” (185). The contrast with “ὑψίπολις” shows that the sense is not merely, ‘when a man breaks the law he becomes an exile’ ( Lys. or. 21 § 35 “ἀντὶ ...πολιτῶν ἀπόλιδας”). The central thought is the power of human wit to make or mar the “πόλις”, according as the man is moral or immoral.
τὸ μὴ καλόν, the generic “μή”, such a mood as is not good.— τόλμας χάριν, by reason of (‘thanks to’) his audacity, with “ξύνεστι”, not with “ἄπολίς” (“ἐστι”). In O. T. 888 “δυσπότμου χάριν χλιδᾶς” is not precisely similar, since it goes with “κακά νιν ἕλοιτο μοῖρα”. Others point at “ξύνεστι”, taking “τόλμας χάριν” with “μήτ᾽ ἐμοί κ.τ.λ.”: but “μήτ᾽” should clearly be the first word in that sentence.