I mean, that’s why in any such contested roll between PCs you should have both parties agree to the roll and just see how the dice land? And if they don’t agree to it, they’re free to roleplay it how they wish to. That’s how we do it at least.
I don’t see why you have to call someone’s preference on how to play a “skill issue” though.
So it averages out to being about average in difficulty then.