Alright. If you don't mind I'll give it a try.
First for the good thing. Your game has excellent writing is really engaging. Overall it really has me hooked.
The gameplay inside the house and interacting with the characters is just fine. Yes, you repeat the same event over and over again and yes it could be improved by adding more variety to some of those events or adding more of them in general(how many times a day can I compliment Anna on her cleaning?) but that really is a minor issue at worst. The reality is that, when it comes to this part of the game and especially when you have more girls in your home to add to the random event list the game flows well.
Critically, the constant repeated events serve to make the game feel padded out which is essential to getting the proper feeling of slow passage of time that you need for the purpose of realism. Unlike many developers that fall into the trap of quick fixes you understand that the sort of trauma the girls have been through is not something that one can cure in a fortnight over a couple headpats. And your gameplay gives us the experience of living inside the house with the girls and slowly building up that relationship as you realistically would, slowly getting them to trust you over a long time and eventually, hopefully helping them find happiness.
However, when it comes to plot relevant events you have a problem. And that problem has to do with the way they are accessed. In particular a lot of content is essentially undiscoverable through the natural flow of the game. Allow me to try and explain what I mean by this.
Your game has two types of events, repeatable and plot events. And there seem to be little to no direct triggers for any of them. They both rely equally on being in the right place at the right time AND rolling the right dice. Or at least that's how it feels from a player perspective. And that means that realistically the only way to get an event to trigger is to enter an area enough times to roll the dice right. This can be once, but it can also be tens of times or worse.
And fundamentally this is a problem. And it is a problem that is directly proportionate to how specific the conditions are for that event to happen and becomes extreme if it is to happen outside of the house.
You see, when playing inside the house there is always something to do so you will be clicking around those rooms a lot. And this manages to ensure that, for the most part, unless an event has very specific triggering conditions that aren't common the player will stumble upon it eventually. And whilst this is less than ideal at least you know the player probably, possibly won't miss out on the stuff.
But when it comes to all the events that happen in the outside world things are drastically different. Fundamentally, there simply isn't enough content outside of the manor to get the player to click around that much. And I don't imagine there could be without distorting the flow of the game and pushing it far away from the core which is the mansion and girls.
What this means is that during the normal course of gameplay odds are very high that the player simply won't run into a lot of the possible events and characters simply because he isn't naturally triggering those areas enough times for it to randomly happen.
Take for example the event when you meet the girl who wants to jump off a bridge in the middle of the night in the rain. That is arguably a critical plot event. After all it's how you unlock a character. And one whose writing and execution are fantastic. But it is also an event that took me at least 20 attempts before I got it to trigger when I was grinding for it.
Is there really enough of a reason for the player to ever be driving to town at night in the rain? Let alone to do so again and again and again until it randomly triggers? The answer is no. In fact, I would argue that there is no reason for the player to do so even once organically. And definitively not so many times to randomly stumble upon her. And this means that realistically, unless you know the event is there and grind for it you just won't get it ever. And you WILL miss that character entirely.
What all this means in practice is that effectively your game relies on the player constantly having the wiki open in another tab to look up events and than grind for them. And that is suboptimal. In fact, I would go so far as to say that grinding for events is quite unfun as well as immersion breaking. Ideally, the end goal of any story driven game should be to produce a game where the player can get to see all the events without ever having to look things up.
My suggestion for correcting this would be to introduce several changes. But they all boil down to basically making your plot events more like a quest chain. Much like you did with Bubbles.
To go back to my previous example. Instead of having that event trigger randomly when I go to town in the night during rain, something that is rarely or ever going to happen on its own have it be a quest chain that starts inside the house. Have something happen at a random night when its raining that gives me a good in game reason to be rushing to town in the middle of the night during a storm. And when I comply, add a 100% trigger that ensures that event will happen on the way back.
And if you want randomness in when the event triggers this is where you put it. You put it before this initial event and in a place where the player has a much higher probability of triggering it. And ideally, you would have some set of conditions that eventually forces it to happen anyway. Like a timer or a timer + certain girls present + other stuff. Or at least gradually push the odds up on a timer. Something so that the player can't be completely screwed out of it by bad luck.
Hope this is helpful. I tried to be as detailed as I could.
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