It's a idea, from Silent Hill Shattered Memories.
We can have some events in the beginning of the game to "learn" about the player.
Then, based in those choices, conditionally show or not some descriptive texts.
Shattered Memories "learn" about sex and alcohol for instance, and change clothes, add items to the scenes, add CGs, etc.
I liked a lot the idea.
I think it's a cool idea. Shattered Memories is one of my favorite games of all time because of this. You can design the choices in your VN so that it is essentially a personality test, then slowly make the game more and more specific to the personality of the person playing the closer they get to the end. I also think it is a good idea if you have something to say about the different personalities at the end as well.
Shattered Memories called you out at the end for being a pervert if you did certain things. If you stared at posters of scantily clad women for a long time, stared at nude art, called phone numbers on bathroom stalls for a "good time", picked up and investigated an NPC's panties even though it was unnecessary, etc. The best part was that a lot of those things didn't even have prompts, so you had to actively rotate and zoom the camera to stare at a poster for a long time, etc. When the game called YOU a pervert (not the character you were playing), you really had no defense. And it was subversive and great.
Every other Silent Hill game was about the town morphing and getting into the protagonist's head - Shattered Memories was about the town morphing and getting into the PLAYER'S head. Brilliant all the way around.