I think it depends on the roll. For two players against each other it’s a bit more fun, but dm/player feels imbalanced, even when it’s character based. Th player winning might feel more fun beating another character with wits but that doesn’t work as well imo for luck, strength, or against something inanimate. It also moves success into a personal skill of the player vs the dm. I don’t agree that it’s necessarily fair.

Perhaps it’s just the feeling of “I took a risk and it didn’t work” vs “I chose badly and was outsmarted by the dm” seem different to me in an important way.

You could reframe this all easily as well for “I’m thinking of a number between 1 and 100, guess it within Y distance to succeed”. That’s mathematically equivalent I think, if you allow it rolling around.