I just played through the entire game for the first time several days ago, and I thought I'd quickly write up my thoughts and share some things I noticed about it as a complete newcomer to this great VN.
First off, the thing that really jumped out at me is how many of the characters have actual personalities and real mannerisms that bring them to life. Like when Charlotte had a lingerie shoot, so she was wearing loose clothing that wouldn't mark her skin. Or Emma learning how to model shoes, and her Mom demonstrating the proper poses for that. The love and warmth Charlotte shows her daughter at the supper table, and how she almost glows when she smiles after tickling Emma for disparaging the food. In fact, all of the light-hearted tickling scenes between Charlotte and Emma are so well done that I think I would enjoy a VN of just them together. Now I'm imagining a mod for Hillside: No Sexual Content – Tickling Edition.
Those small interactions add a lot of verisimilitude to the world and really go a long way in making the reader care about these people and their lives.
I have also found myself somewhat averse to considering Emma as a love interest, and just wanting to protect her and keep her safe. I think this is partly because she acts so childish and appears younger than her stated age, so it's natural to just want to be professional and behave as a security guard towards her. In that way, the MC becomes very relateable to the reader, since his internal thoughts and dialog also constantly drive that motivation home by repeating "Emma's safety is the priority" again and again. As the story progresses, however, I think her growing understanding of her own sexuality will make her appear more womanly, and that along with the resolution of the threats against her, will all let this abate naturally and there won't be so much of a "creep factor" when interacting with her. Hopefully that can happen without it becoming forced and the MC – and reader – feeling conflicted and
in conflict (with Charlotte and others) over forming a relationship with Emma.
The other part of this aversion to pursuing Emma though is a bit more insidious and pervasive, as it is tied up in all of Charlotte's past trauma and distrust, plus the sleazy fashion and entertainment world that is Hillside, Kaylah's assault, Suzi's blackmail, Emma's stalker-filled school life, and more. Without dwelling too long on the details, I'll summarize it with the phrase "White Knight Syndrome", except that Hillside has begun as a more pathological variant of this mental condition called "One Good Man Syndrome" (which is a less well known term compared to "White Knight Syndrome"). The world perceived by the MC reflects back the belief that he is the
only good man to ever exist in the world – past, present, and future – and that all other men are only threats and evil. I believe the key to this, strangely enough, is Steve. If he were written as just a normal friend, perhaps of the "You've got a female client? Is she hot?" and then "Nice. *nods approvingly when he finds out she's a supermodel*" variety, instead of a hypersexual, over-the-top pervert who acts suspiciously, a lot of this problem could be avoided. Basically, I feel what this story needs as it progresses are other decent men to appear who are important characters. Otherwise, I worry that any relationship with Emma or Charlotte could end up feeling to the reader like the MC is just deluding himself into thinking he's any different from every other evil man out in the world, and further establish that unfortunate "creep factor" in those desires.
Another interesting thing to me is how the VN is written only using dialogue (spoken and internal), without any description of activities, and yet what is happening is mostly clear to the reader from believable and well-rendered visuals and context. There are a few times when the time skips are slightly jarring, but all in all it's a good lesson in how "show don't tell" is a powerful tool in creating a seemingly real fictional world.
The choices and gameplay are also quite natural, and don't feel too forced. You can imagine the MC choosing either option, and there isn't anything too OOC that breaks immersion. Some of the choices are not easy to figure out either.
Hillside is definitely one of the more well-written and polished stories out there, and it's refreshing to not have spelling mistakes every second sentence like in some lazier VNs.
That's about it for initial thoughts. I'm looking forward to more and seeing what happens next in the story!