It seems so natural now you translated it, but the thing with もの is that I never know which one it is - does it mean person? thing? is it the particle indicating reason? part of a number of grammar points with all kinds of different nuances? I’m sure easier understanding will come with frequent exposure to it, but for now it often perplexes me.
An amusing example of もの’s vagueness: I fed a similar phrase, 知らぬ者はない, into Deepl to see what it would come up with. Deepl had this to say:
So helpful, Deepl, thanks. 
Your interpretation seems fine to me.
As many people had asked her that before, she thought ‘again?’, but given that this was a well-known wealthy man she couldn’t just curtly refuse him, so she was more than a little perplexed.
だけに means “given that” among other things.
Basically she wanted to refuse him, but because he’s rich and famous and important she feels pressured to accept and isn’t sure what to do, is how I understand it.
This is one of those lyrical description sentences that I tend to skim over. I think the subject is the harbour itself, filling the sky with a faint, lonesome (or something, not sure how exactly to translate this) light, but the blind boy couldn’t see this.