After working on yet another playthrough to chase the ever elusive variables-not-chosen, I just realized something unintentionally amusing.
During the date with Jill in Episode 4, she is surprised and excited when the learns the MC doesn't know she's a Royce; as she says, she never knows anyone's intentions due to her family being so important.
But during the flashback at the start of Episode 5 we see that Rusty also didn't know who her family was, and in that case Jill didn't much care. In fact, she quickly revealed her pedigree to burst his bubble.
I don't think this is contradictory per se, since she also says the MC was refreshing for not talking about his bank account and Rusty fell straight into that trap! But it does make me wonder just how many of Jill's suitors really did know specifically that she was a Royce (rather than just that she was wealthy).
I also wonder if part of the reason she agreed to a date with Rusty was that he did show interest in her before he knew who she was.