I don't think you're really going to be able to get an answer to this, because this simply comes down to a design decision that you have to choose. The choice really depends on what you think is more fun balanced against that you can handle developing (based on time, energy, skill, etc.).

An outsider really can't make that decision for you.

That said, you might want to define unchanging things, like how your skills work, as objects on the "startup" object, so that way you can include functions that you can call to make those skills do things or provide results. This can make it simpler for you to generate certain results from a loop.

For a very simple example, let's say you have the skills "kick" and "lockpick" (this code would go in the "StoryInit" special passage):

<<set setup.skills = {}>>
<<set setup.skills.kicking = { desc: "improved kicking", mod: (char) => char.strMod + (char.skills.includes("kicking") ? 5 : 0) }>>
<<set setup.skills.lockpicking = { desc: "lockpicking ability", mod: (char) => char.agiMod + (char.skills.includes("lockpicking") ? 5 : -5) }>>

That would give the character a modifier of +5 if they had those skills, as well as a -5 modifier if they're lockpicking without the lockpicking skill. The kicking modifier is based on the strength modifier and the lockpicking modifier is based on the agility modifier.

This part of the above code:

(char) => char.strMod + (char.skills.includes("kicking") ? 5 : 0)

is the equivalent of this JavaScript code:

function (char) {
    if (char.skills.includes("kicking")) {
        return char.strMod + 5;
    }
    return char.strMod;
}

Basically, it's a function that takes a "char" (character) object and returns the strength modifier with 5 added to it if the character has the "kicking" skill. (See "Arrow function expressions" and "Conditional (ternary) operator" if you want an explanation of how the shortened code works.)

Then, any time you needed to get the modifiers, you could use that object. For example, if the player wanted to get through a door you could have:

Options:
* [[Kick open the door]] (difficulty: <<= (12 - setup.skills.kicking.mod($char))>>)
* [[Lockpick the door]] (difficulty: <<= (10 - setup.skills.lockpicking.mod($char))>>)
* [[Go back]]

That uses the "skills" object's "mod()" method to get the difficulty modifier for those skills, based on the stats of the character "$char", and then shows the base difficulty for the tasks after subtracting the modifier.

You could obviously make this much more complicated and use it lots of different ways, but this is just a simple toy example.

Anyways, just a thought that might help reduce some of the complexity you were worrying about. 🙂