Case D) -1 AC (save ends) (save ends)
Multiple penalties usually stack, unless they come from the same named element. In that case only the worst applies.
In the same manner multiple auras from two exemplar of the same creature don't stack their penalties, so multiple instances of the same weapon property (even if applied from different weapons) don't. However, each effect carries its own save ends duration, so using two withering weapons helps in keeping the creature's AC at bay.
The creature is affected by the two eithering effects simultaneously. Each effect is kept separately, so they could independently increase their penalty; however, only the worst penalty applies.
| Withering | Withering | Total Penalty
ROUND | Longsword | Dagger | to AC
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1 hero | hit (-1 AC) | miss | -1
1 foe | fails | | -1
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2 hero | hit (-2 AC) | hit (-1 AC) | -2
2 foe | saves | fails | -1
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3 hero | miss | hit (-2 AC) | -2
3 foe | fails | fails | -2
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4 hero | hit (-1 AC) | hit (-3 AC) | -3
4 foe | fails | saves | -1
Each time the foe saves against one of the two effects, the penalty to AC caused by that effect resets.
I'd suggest to use two different dice to keep track of the independent AC penalties, removing the relative die each time the foe saves against that effect.