Since I have just started a Sage run I'd like to touch on something in the early scenes. In C3, when MC stays the night with Jill they have that conversation, bringing up the usual My Mom died while giving birth sob story (just for context) when Jill comments on him being from poor upbringings that all this ornamental dresser and nice bed are nice and all, but she could do without.
While this is true in theory, I call BS on it. Of course she has her own traumata with overbearing parents and her dead sister, and later on a creepy, but castrated one-sided love interest, one thing she never went through is being poor. Essentially she doesn't know a single thing about it, and thus can't know if she could live without.
[As a speculation for an eventual continuation of my old Jill run that is stuck after C8 on my old hard disk, I feel that the main obstacle to overcome will be that Jill's parents would never accept the MC coming from a "lower class".]