Imo, any game that doesn't just tell the same goddamn bog standard story deserves an award. The (comparative) rarity of those honestly shows how creatively bankrupt the genre is.
The problem with that is that "Originality" Doesn't get funded most of the time. If a person makes a totally original / creative story then a lot of times you won't get funded.
It's much easier to go with:
"Alright so here is the deal. We are gonna do a harem. Dad is dead, or in prison or whatever who cares. The 3 main girls will be a cute and clingy younger sister, a bitchy older sister that will eventually come around, and a mom that loves yoga and wine."
(This is like 50 different games...)
Isn't writing subjective though? You may like it, some may like the other writing styles. Still, it was the first time that this was hosted and people are already giving feedback to make it better next time.
Can't fight against popularity though. HS-based games are famous for getting a lot of player base, I am not a fan of that type of design but I must admit. Their lewd rendering is top notch and Daz falls a bit short on that.
Also, if it eases you a bit; the games that won will not be featured in the next award ceremony. Other games will have a fighting chance and help broaden the taste and vision of fellow players.
Technically everything is "Subjective", and it is hard to "Objectively" say X is better than Y unless you are looking at it from a purely technical standpoint.
The reason why I think ORS has the best writing is:
The characters are all realistic with unexplored depth. Minor details are accounted for. It's done with 2 protagonists that must switch back and forth and the timeline must be carefully kept track of to account for the actions of multiple protagonists.
You can get a lot more content on multiple playthroughs, and you can't get everything on a single playthrough. It allows for a certain flexibility of character to be able to play the way you want to.
If I want to be a Chad & fuck all the women, and have Lena be loyal and faithful to me. The game does that...
If I want to play as a cuck and have Lena take every dick in town while she teases me. The game does that