Depends on the type of game. Pure VNs I usually don't because they're too linear so there's not much replay value. Once I've won the game once or twice there's no real reason to replay it unless it doesn't have a gallery until enough time has passed that I've forgotten enough of it for at least parts of it to feel new again. Normally I would just open up the gallery and replay some of my favorite scenes if I wanted to see them again. Kind of like reading a good book. I'll probably reread it, but I wouldn't read the same book twice back to back. I'd wait a few years.
I could still really like a pure VN, just probably wouldn't play it more than a few times. Something set up to be more nonlinear that has different options on how to achieve different goals in the game I'm a lot more likely to replay. So a game that's set up more like an RPG for instance would have a lot more replay value.