Math on low-roll wins vs blackjack...

With the example given and the spread in skills, I’m perfectly fine with low wins because the higher skill is still winning a great deal more than the lower skill. I don’t see a particular reason why the difference should lead to an overwhelming difference (9:1) in win rates when substantially (3:1) is enough.
The more interesting question would be: are there any cases where the lower skilled character’s chance of winning ever exceeds the higher skilled character’s chance?
 

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I agree.

I’m not sure what you mean. I don’t see either one as more or less playable.
two factors...
1) Roll low = better is more consistent with Nat 1 = Critical. Keeping directions the same is a simplification (a minor one, but still a slight easing of required memort
2) lower skill losing less makes low skill less punishing on players; in case you're not aware, PC's have a lot of low skills in DB...

Both issues making the game easier to play, even if slightly, at the expense of realism.
 

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Simplified it down to d4 to make it more understandable, but a 20x20 table would look similar. Let me know if I made any mistakes.
 

The more interesting question would be: are there any cases where the lower skilled character’s chance of winning ever exceeds the higher skilled character’s chance?
There can be systems where a low-skilled person's proportion of critical successes exceed those of a more skilled character. If I need a natural 20 to hit that dragon, all of my hits are going to be crits!
 


There can be systems where a low-skilled person's proportion of critical successes exceed those of a more skilled character. If I need a natural 20 to hit that dragon, all of my hits are going to be crits!

Oh I've been searching for the right analogy here and that's perfect! "If you have a lower attack bonus more of your hits will be crits (in D&D)."
 


Which brings up another question. Are crits 1 or 20 in a high roll system? I'm assuming crits still beat regular successes.
In the context of Dragonbane, yes, a 1 is still a crit and a 20 is still a fumble. You're not fundamentally rewriting the game, you're just looking for highest roll without going over in this one niche case.
 

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