Will Cindy still be stingy and expect Ian to pay for everything and to go out clubbing, or will she use the self-introspection she gained to try to be a better person?
Given Perry's loyalty to Wade, I could see the Cindy path having Wade/Perry/Jeremy abandon the "piece of shit" Ian and Ian goes from drinking at the Fortress to doing mostly "couple things" with Cindy like hitting Blazer and Shine or spending the day going to Pier One Imports.
Even though it involves cheating, I think the Cindy path most represents the "growing up and moving on from your high school years" path, with Ian leaving behind his toxic friends and doing things that most 20-somethings do like clubbing instead of playing video games and getting drunk.
Might depend on Ian? Chad Ian could very much match the expensive lifestyle, especially if his profession provides the funds to keep up a lifestyle of some splendour. I would argue though that Cindy isn't a bad person for enjoying clubbing and such, her and Wade clashed because neither of them were very good at seeing the other's point, and in that way I guess Cindy could perhaps become more considerate of Ian's other interests.
But I guess this might also depend on his friendships, I imagine Wade and Perry won't be available to hang out given the group's history, if we even see them become aware of the Ian/Cindy couple.
With Jeremy coming along for Billy's party, Mike in the gym and Axel possibly becoming more friendly, I could even see Ian having the option to surround himself with a new composition of friends and bring Cindy into those friendships more.
If Eva decides to meet popular demand for Cindy/BBC I could even see this route be where that happens if Ian is just her friend or another sexual route like cucking or sharing opens up with her too.