>Why should jumping from one
Because it's not the same task. After 20 sessions, the characters' skills have advanced so far that the exact same task that would have challenged them in the first session is hardly worth rolling for now. So there's no point including it in the story.
In Session 20, a challenge sufficient to stretch and test the characters' skills must be level 6w - so it's up to the narrator to describe why jumping from one roof to another is harder. Maybe the character is attempting a longer jump than he would have dared at first? Maybe there are extra environmental hazards to overcome this time? Maybe this time the bad guys are firing crossbows at him?
If the narrator really can't justify why the resistance would be higher, then just say "okay, you jump the gap easily" and then immediately come up with another challenge to fit the story that does have a resistance of 6w.
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