The date with Lily was really nice and showed how she can simultaneously be fun, clever and sexy. However, I didn't get the point of Mabel being present beyond adding a slight bit of spice to the proceedings. There was no actual trade-off to be made there - the choice is between going through the date smoothly, or fucking things up completely with Lily. It's not like you can actually do anything with Mabel in that scene if you deliberately choose to fuck things up with Lily. It would atleast have been an interesting trade-off if it gave you the option to progress things along with Mabel, especially because to my eyes Lily and Mabel are the hottest girls in the game.
I have always believed Bella or Jolina (or both as a team) to be the gold diggers, so I never pursued them in my canon playthrough. But for shits and giggles, I did a quickstart choosing casual relationships with both, and invited both to the beach-house. The ensuing scene just seemed to me the both of them tag-teaming to make the MC a massive chump, playing him like a fiddle, lying to his face.
MC is so young and has his whole life ahead of him, same for both Katie and Jenna, so even if he feels strongly for them, 10 years is really nothing in context of a lifetime of financial security the inheritance could provide for all of them. He can simply resume his life with them 10 years later, and they will all still be young, while having 5 to 15mn in the bag.