A lot of people have made that point. The story of his Mom is likely to be something that will come up when he's with Jill because there are some parallels there, and it could help her to realise she can reject her family and their wealth to be with him, but it seems a little too formulaic and obvious so I'm sure there will be a twist to the tale that won't make it so similar.
Personally, I hope that Jill's eventual character arc will be something other than learning she can reject her family. In part, because that is rather cliche at this point, but mostly because Jill seems like the sort of person who already knows that. Not that she would *want* to run away or anything, just that she seems comfortable standing on her own if it comes to it.
It's interesting in that we don't see Jill's family at all; Tybalt is basically forced to do double duty as both the insufferably aloof rival AND the stuffy, controlling family. But while Jill respects Tybalt (probably more than is warranted), she is not hesitant to countermand him when he steps out of line.
Jill's only other authority figure is Bella, who generally seems to be in favor of the MC dating her once she establishes he's not an unrepentant DIK. While Bella has a (long) list of concerns over the MC she would gladly summarize with her trademark deadpan glare, his 'common-born' status has never come up.
It makes me wonder if Jill's story is going to go somewhere different. It would certainly be amusing if, when the MC learns just how rich and powerful her family is, *he* is the one tempted to treat her differently and the struggle is to get back to treating her as a beautiful girl who cares about him.
A hope we have for so many games.
Too true.