Do you like to lose?

It’s this one, I believe. I’ve added another option in my local version which will go up at some point; when I do my draft revisions it’s something I’m going to check through - the four-option choice sets that test opposed stats don’t tend to have overlap, which means someone with bad luck has a small chance of not having any of the required stats above/below 50.

Agreed, this can really feel miserable!

I think this makes a lot of sense. My experience doing choices that include die rolls in non-ChoiceScript games is that you have to make it very clear how difficult the choice is to succeed before taking the choice - I’m thinking of something like Fallen London or the Sunless games - because if you don’t, it feels unjust and you also lose the excitement of succeeding at a near-impossible roll.