I think that since the rework Ian is not quite as dependant on Lena for his connection with Ivy, most of his interactions with her are actually thanks to Jeremy (chapter 2 introductions are because they were greeting each other, chapter 5 Jeremy invited them to the Blazer for some drinks on the house when Ivy was poledancing, chapter 7 Ian was at the bar with Jeremy before they meet Jess, Ivy and Axel). Even this new wrestling scene happens (according to Ivy) because Jeremy had promised to teach her some fighting moves but since he didn't show up she ends up hanging out with Ian instead.
Now it could be argued that Ivy showing any interest at all on Ian is because of his connection with Lena, but she doesn't seem to be that unapproachable even with people like Perry or Wade so that feels like a bit of a stretch. Even this necessary relationship boost from confronting Axel with the truth was less about Ian being with Lena and seems to be more about she being impressed that Ian had the balls to play it straight with Axel. The issue is just that without being dating Lena, Ian has nothing to confront Axel about so we miss this chance to impress her and end up being 1 point short of enabling the wrestling scene. The fact that this essentially means Ian needs to have had a relationship with Lena feels more like a side-effect of the check requiring you to have impressed Ivy in every meeting rather than the reason for it.
I can see your point, especially about the Axel confrontation point which won't happen without the Ian Lena dating check.
What I'm arguing is from Ivy's pov though. Lena and Ivy talks often about Lena's guys. So if Ian is not with Lena, Lena doesn't talk a lot and not favorably about Ian. From that lens, it makes sense that Ivy's interest in Ian is significantly less than if Lena talk about him a lot.
You're right that that doesn't excuse the Ivy Ian gym scene to not exist because the catalyst of that is Jeremy inviting her, which should happen regardless.
But I think from Eva's pov, at least from my read of it, there is 2 different "version" of Ivy, the one that goes to the gym (and thus meet Ian), and the one that doesn't go to the gym.
Just like there is 2 different "version" of Jessica in the game.
Yes it doesn't make the perfect sense and you aren't wrong when you say it's stingy, but Eva's previous game is also like this where some scenes are just unattainable based on previous early decisions.
I seriously would not realized there is a Dad depression path on GGGB if not for JDMOD, and this is long after I finished that game.
One thing we know of Eva though, she's malleable to criticism. So there is still a chance that future updates will be less stingy and more generous for the paths.
I didn't play the version before the remaster but some character has a different skin color and some other character has different appearance too or something like that? I feel like those changes, viewed from outside perspective, makes it "seem like" Eva is malleable to critics. Though we can never say that for sure of course.