If Cherry and Lena reconcile, do you see something happening between both of them?
It's a porn game so why not. The hardest part is that, at the moment, even trying to push Cherry towards reconciliation requires Ian to still be sleeping with her (incompatible to being in a relationship with Lena) and it loses you a relationship point with her.
The funny thing is that Ian can have the "ian_cherry_love" switch in his relationship with Cherry and then reach the Holly+Lena throuple by the path of dating Holly instead of Lena, but idk how that timebomb is gonna go (extra funny because you can have had Ian buy a necklace he was planning to give to Cherry upon her return from her trip).
Prayer circle for the route where Ian achieves the harem with all the artist women, Holly the writer, Cherry the painter, and Lena the model/singer.
Not sure how Ian's Lis are so much better. Other than Holly who is also available to Lena, all of the LIs are flawed in one way or the other
Different degrees of being flawed and Ian LIs are usually at least repentant or more complex over their flaws.
If Ian doesn't sleep with Alison she moves on or at most tries to make him a bit jealous. If Lena doesn't sleep with Robert he gets her fired from her job despite potentially promising to have her back.
Cindy gets a really long arc building up her dissatisfaction and feelings of stagnation with her life overall and her relationship with Wade, her cheating isn't excused but at least you understand there was more to it than her just being horny. Mike cheats on his gf with Ivy and potentially Lena because they are hot.
Cherry genuinely feels like shit about what she did to Lena and actually puts some distance between herself and Ian if he is with Lena. Axel has his whole "so sowwy

" routine and trying to get Lena back, but will also be pursuing Cindy just to get his dick wet, doesn't stand up to Seymour or Agnes when they decide to use the two of them as meat toys for their weird elderly kinks despite knowing how uncomfortable Lena was, and goes around punching people just because they were close to Lena.