Some quick analysis avoiding the complications :-) (Most significantly I am only counting extra victories - that underrates the advantage of improvement because it ignores other improvements)
Allowing for ties, the chance of a victory with equal numbers is 190/400
Improvements in ability shift the chance of victory for the better side as follows
+1 1/400
+2 3/400
+3 6/400
+4 10/400
(i.e. triangular numbers)
Until you hit 20 as your target number - which is the same as 19.
When mastery numbers are different, criticals matter too, favouring the weaker side. Then it looks like the actual numbers start to matter more
Explanation:
With equal skill the chance of a tie is 20/400 (both roll the same number).
The remaining 380 results are divided 50/50, victory/defeat
If the opposition rolls lower, and Succeeds the hero still get a Marginal Defeat, even rolling Success instead of a Failure. So we don't need to consider rolls where the opposition Succeeds. If the opposition rolls higher the Hero would still get a marginal victory, even with a Failure. So we don't need to consider rolls where the opposition Fails and rolls higher.
So the only rolls that matter for this analysis are those where: 1) The Hero rolls a number that is now a Success instead of a Failure. 2) The opposition rolls a failure that is equal or lower to the Hero's roll.
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