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> By the way, Singleton isn’t the only one who translates the passage as
“dusk”, so I’m confused as to why he (and others) did that if it’s as
straightforward as saying that  “sera" is "evening."
>
That's a good point, Steve. "Sera" is *also* 'evening', and 'evening' is the
most obvious translation for 'sera' when one is learning English. In
Italian, 'sera' spans semantically from 5pm to when it's totally dark.
Anyway, here's what I found in the glossed edition I used in high school, by
G. Giacalone. It's one of the best editions that are used in Italian
schools, as it was first printed in 1997. I'll translate the passage for you
(it's a footnote, p.319)

18. come suol: 'as in the evening, during the new moon phase, one is used to
look at another'. Comapre to Virgil, Aeneid, VI, 268, "Quale per incertam
lunam sub luce maligna Est iter in silvis". The classical reference makes
the situation more solemn, also reminding of Dante's experience as a man
connected with the life of his 'comune', to the dark streets of the medieval
city, to his artisan memories, first the 'maestro' (which in the Bandi
Lucchesi 134 stands for 'artisan'), then the taylor. By recalling the city
life in Florence, the environment and landscape anticipate, we might say,
and condition the theme of the Canto, which is fully concerned with the
memories from the poet's youth and his remote hopes, through his talk with
maestro Brunetto Latini.

...Now, I'll look more into 'sera' and the meaning it might have there and
in Dante in general. But you have to wait, for I should leaf through the
historical dictionary of the Italian language, which is at university, and I
won't be able to check until Monday morning.
Best regards,
Sara