So here is the skill challenge adventure generator.
For an inn.
Standard loss: 1/2 a random treasure parcel (1d6+4) of the inn's level.
Standard opposition: If the trouble is formed by some group, that group is comprised of enough creatures to create 1 encounter of the inn's level - 1, 2 encounters of the inn's level, and one encounter of the inn's level +2. The leader is a character of the inn's level +4.
Resolution of trouble could just be a single roll or an adventure in itself.
Random Sources of Trouble
Source of Trouble (1d6)
1 - Labour unrest
2 - Criminal activity
3 - Disaster
4 - Government/law enforcement
5 - The supernatural!
6 - Roll twice
Labour Unrest (1d8)
1 - Union trouble. A new hire has convinced the other workers that they are being exploited - not getting paid enough, not enough free time, no sick days, no benefits, bad work conditions, etc. The workers quit, perform their jobs poorly, act surly to customers, etc. There is a 50% chance that a suck-up among the labour force will secretly report to the PCs about the activities of the rabble-rouser.
Failure: Standard loss as the workers react poorly to the PC's attempted method. If this roll ends the skill challenge, the workers may go so far as to attempt arson or assassination.
2 - Death Cult. One of the workers has recently lost a family member to the plague. Without enough cash to afford the proper rituals, he was forced to go to a new temple worshipping something called The Grey Veil. In actuality it is a death cult dedicated to Orcus attempting to infiltrate the settlement. In return for the rituals, the worker is being blackmailed - to preach the word of The Grey Veil, to steal from the PCs, and to report any information on the PCs to the death cult.
Failure: The inn is infiltrated with worshippers and becomes a meeting place for the cult. They perform foul rituals in the inn while the PCs are away. Or perhaps the worker stands up to the cult and is killed, and customers stay away, creating a standard loss. Either way the death cult doubles in size! If this ends the skill challenge, the cult takes violent action against the PCs and claim the inn as their own.
3 - Shapeshifters/Mind Control. The workers are being replaced with shapeshifters - dopplegangers, succubi, oni, etc. - or are being controlled by some outside force - lycanthropes, aboleth, mind flayers, alien mind control worms, etc.
Failure: The PCs are unable to stop (or perhaps even discover) the invasion. If this ends the skill challenge, the thralls will attempt to turn/enslave the PCs.
4 - Competiton in the Labour Market. A new inn has opened up down the street and is offering better prices/benefits/etc. for its workers. The PC's inn's workers are leaving for greener pastures. What's worse is that the other inn is run by a criminal organization.
Failure: The PCs suffer a standard loss as they are unable to stay fully staffed, or they must hire poorly-trained workers to fill out their staff. The inn gains a reputation as a dump. If this ends the skill challenge, no one will work at the PC's inn - they are being threatened by the criminals who run the other place.
5 - Madness. One of the workers goes insane from a curse. He plots murderous acts and rambles to himself.
Failure: The worker's madness unchecked, he goes on a bloody killing spree. The inn must be closed down and gains a bad reputation. Loss is double standard! If this ends the skill challenge, he attempts to burn down the inn or kill the PCs - and his curse may be transferred to one of them...
6 - Romance. One of the workers falls for a PC.
Failure: It's a bad breakup, the worker feels scorned, is crazy jealous, or just crazy. At any rate, this affects work; the PCs suffer a standard loss. If this ends the skill challenge, the worker makes a deal with infernal/demonic forces to curse/kill the PC.
7 - ??
8 - Roll Twice
Criminal Activity (1d8)
1 - Extortion. The local organized crime faction moves in on the PC's inn and asks for "protection" money.
Failure: Standard loss as either the PCs pony up the cash or have to deal with broken windows, thugs harassing their customers, employees afraid to come to work, etc. If this ends the skill challenge, they torch the joint.
2 - The Black Market. It seems that the PC's inn has a reputation for being the place where you trade illegal goods. Rightly so, too. People are fencing goods, selling illegal drugs, making contracts for assassinations, trading necromantic rituals, etc. in the inn.
Failure: The PCs are charged by the local law enforcement with all these crimes. Bribes and fines make up double standard loss! If this ends the skill challenge, the PCs will be arrested for exectuion or exile. Note: it is possible the PCs profit from the black market activities; if so, they receive 1.5 times their normal profit! (Bribes take up some of it or it would be more.) However, they may draw the ire of any organized criminal group, and the more militant law enforcement groups (Paladins of St. Cuthbert, for example) may come down hard on the PCs.
3 - Murder. Someone involved in criminal activity killed a person of import, and brought the corpse to the inn to hide it.
Failure: Authorities discover the body and shut down the inn/question the patrons/the inn gets a bad reputation. PCs suffer the standard loss. If this ended the skill challenge, one of the PCs was the one who was killed. Just kidding! (Unless it's an Epic inn.) No, in that case, the authorities will shut down the inn indefinitely.
...more later.