You're doing it again, ILS! A strong. engaging plot with characters and relationships which feel real. No 2D stereotypes to be found here, and no boring mc. Just as in Now & Then, the mc and his story are central to the narrative, making the game so much more enjoyable by giving it real meaning. I can't wait to see how this turns out.
However, I was moved to leave a comment because there are two glaring issues that I think need to be addressed. The first is that you can't complete all the girls' events in one run! Obviously the player will want to see all the events - they are central to the game - and obviously you want the player to, so why would you prevent that? It's not like you are expected to do an X run and then a Y run for each girl or ending, like in Now & Then. On the contrary, the dialogue seems to expect you to progress with all of the girls! For example, the mc was talking about visiting Roe's home even though I hadn't had "time" to do so. After reaching the end of the update and realising I had been forced to miss a number of events, I had to load up a previous save to play them, in which I hoped I was far enough back that I still had "time" to do them all. But this didn't feel "canon", because in my head the mc would of course progress them all. Please consider rectifying this.
Secondly, the mc is again cracking awful jokes and references during the sex scenes. This was easily the worst part of Now & Then, which was otherwise a brilliant game. Jokes during sex are almost always a turnoff; they pull you out of the mood, and I find myself trying to quickly skip through them so I can enjoy the scenes. There aren't many sex scenes yet, so this would be a great time to change the writing here.