You're exaggerating the problem. Throughout the season, Tremolo has been asking himself who he should stay with. Yes, it was really implemented in the end quite crumpled.
But how was it supposed to be done? You ,guys, have too high expectations for the game and the engine having serious technical limitations. The funniest claim for me is that the сhoice system doesn't always work. Certainly. Not in all AAA-class games does the choice system play a role at all (we will recall the Mass Effect), and in such a technically backward engine as renpy, it was apparently not possible to implement all the variables and make a different path for each solution. It's a lot of work. The work already took 7 months, if hundreds more variables had their own variables, everything would have been confused in a heap.
Sure, choice is always going to be an illusion, but it has to be a
good illusion. The MC did indeed keep questioning his own behavior in Season 2... and then went right back to whatever he was doing. He never actually took any of those questions to heart. Then one morning Heather compares him to Tommy and suddenly he has a "revelation." That's what creates the disconnect and ruins the illusion.
I understand there will always be resource limitations, but that's part and parcel to being a game designer. You need to save your powder for the most important choices first and foremost. To continue the Mass Effect analogy, the decision to limit the ME2 teammates to a single side mission apiece (rather than being part of the team) in ME3 was a shame, but a good allocation of resources. The decision to limit the ME2 teammates to quick holo-cameos before the final battle was a more questionable allocation of resources. The decision to end the trilogy with a simple Red/Blue/Green choice of poorly explained options has to rank as one of the worst allocations of resources in video game history.
We're nowhere close to Mass Effect 3 here, thank heavens. Still, this episode was called "Crossroads;" choosing not to spend resources fleshing out those diverging paths is a highly questionable move IMHO. If DPC wasn't willing or able to handle all the options he had written himself into, it would have been better to scrap the idea of a single crossroad and instead allow each path to find its own turning point. For example, Jill vs Bella would be decided after the doubles tennis match. Sage vs M/J would be decided when Sage asks the MC to help her help Maya. That sort of thing. Then let Becky's party be the point where the MC will take stock of his partying habits and decide whether he wants an endless stream of flings or to buckle down and commit to a serious relationship.
We still end up with the MC committed to a path, but now it feels like a progression of his actions rather than directive from on high. I don't think that would require all that much more work than what we got either, and it would flow a hell of a lot smoother. Sure, I'd still be worried about
resetting Maya's subplot and Zoey's roll in Season 3, but at least I'd have a lot more faith in the game respecting and adapting to my most important decisions.