You are correct that those are the challenges to be solved. That could be a good plot how to overcome all those obstacles. For example, they could emigrate to a country which is more relaxed on all those things, like it was done in Sisterly Lust by Perveteer,How, on the solo Haley route, have they solidified their situation? How have they eased the fears of their employers? How have they satisfied society? How have they mollified their parents? How can they have a child without inviting questions they're unwilling to answer?
I believe they could find a solution. IRL people have all kinds of challenges and they deal with them (or not, if they are weak).Yes, but in the milieu they've created for themselves, they can't actually be together.
It is mostly a figure of speech. Quite romantic, if you ask me, though some people can have different opinionsAnd when does he give her the latter, once she asks? Nearly never. Yet another dropped storyline.
For me Haley's Story is the story of the modern Romeo and Juliette. The whole world is against their love but it doesn't mean that it has to have a bad ending.