LostSoul said:
- The town is on fire. Can you put it out in time?
- A mob has formed outside the mayor's office. Will they lynch him?
- Cattle - the lifeblood of the town - are stampeding. Can you round them up, or will people starve?
Important: each skill challenge should be its own conflict. I don't know if the current system will allow you to resolve a greater one ("Save the town") by adding up little ones.
Sure, the DM willing to put in more work can adjust the outcome.
If they stop the fire with no failures then only the one building was damaged and it was mostly superficial. The more failures they rack up, the more damage the town suffers until, with complete failure, a third of the town has been destroyed.
The more failures they rack up trying to stop the mob, the more damage the mayor's home and the mayor, of course, suffer. Complete success means minor damage to the facade, maybe a broken window, and a bloody nose for the mayor. Complete failure means the mob lynched the mayor, completely destroyed his home, and looted some of the shops in the village market.
For the stampede, more failures means more property damage before the cattle were rounded up with complete failure meaning the cattle tore up the street they were running down, damaging homes along it, tore down the gates and escaped into the area surrounding town. They'll do damage to the crops out there before they're rounded up over the course of a week and in the mean time their numbers will suffer due to predation by wild animals and kobolds.
Just adjudicating each scenario and describing the results should take an entire play session. If the players get lucky and breeze through their dice rolls and save the town they'll be lauded because what could have been utter disaster instead resulted in the urban equivalent of scrapes and bruises. If they fail horribly then a third of the town will be homeless and they'll all be leaderless and at risk of starvation if they don't round up the cattle, adding the possibility of a
fourth skill session as the PCs now have the difficult task of convincing the townsmen to follow their leadership. Since the townsmen saw the PCs make the situation last night worse than it might otherwise have been, that would be a heck of a job. Failure could force them into the wilderness with no hope of succor and only a bunch of XP to console them.
Of course, this is all academic because Wolfwood doesn't want to do that.