You've got some very nice stuff cooking here. I played the game a few times, getting game overs on a few attempts and actually managing to reach the official cut-off on one. The experience was mostly positive, as I appreciated the art, gameplay, and much of the lewd material quite a bit. I did have a few complaints, which I would like to list here in the hopes that they can be improved for the full release:
#1: Dimon is so close to the "entertaining asshole" sweet spot imo, but sometimes he leans just a little too far into "actual sex offender" territory and reads like a bad 4Chan greentext. I recognize that this may be a matter of taste, but it feels like more of an issue because for a majority of the game's runtime, Dimon is completely palatable.
It stands out against the majority of scenes when Dimon actually talks about blackmailing women into sex, or when we get transition text saying he spent the weekend bullying women. The bonus scene especially did not land well with me after playing the full game. Like I said though, matter of taste. You gotta make something that makes you happy first and foremost, so take this opinion for whatever it is worth to you: I would have personally found Dimon more entertaining, as a pervert who takes lewd pics and schemes to sleep with women, if the culmination of his goals weren't non-con.
#2: I found the balance between events and efficiency a little difficult to manage, even while trying to stay on top of things. After a few playthroughs, I could definitely tell what the most effective route was, and I knew what events needed to happen by what times to prevent a bad ending. It's fine if you can't get every possible event in an efficient run, but I think a bit more signposting could be done on what goals need to be hit by what times. The scene you get in a game over where Olga tells you where you messed up is helpful at least.
#3: Bait options. There was never a reason to talk to a character who didn't actively have an event going on, and this is something I only realized by trying to do so. I don't think these should be listed as options at all if the end result is "nothing". Choosing to decorate your room may be functionally useless (as far as I could tell), but it does at least offer a cosmetic change. I'd also, personally, consider the "Dimon's Hobbies" choice to have no value in its current form, although I will concede that if you like listening to Dimon talk, the scene of him reflecting on his hobby is arguably reward enough.
If you want to leave the option to talk to characters outside of events around, I think the best implementation would be to have a few standard events that offer small inconsistent benefits. Maybe sometimes you gain free EXP, other times you get a temporary Search or Sales boost, some you may find bonus Materials, or if you're lucky you might just get a hint about some less obvious photo opportunities (Ones you don't just get by going to an event, like how you can get a pic of Senna by looking for materials at night). Come up with like 3 of those random events for each character, and it becomes a great place to spend any free time you might find yourself having.
That is assuming you have free time though, which admittedly doesn't come up much in the current system if you go to every event offered and are working to collect all the materials you need.
Those are all my thoughts. I enjoyed this little slice of a game, and am definitely gonna be keeping an eye on the project moving forward!