One of the players in the Fortress Eibon games in an incorrigible rogue; he has played a succession of amoral through to sociopathic, lying, cheating, stealing murder-hobos.
Now I consider this a good thing; it's good to have players/characters that give aspects of the game a good thrashing. And it helps keep a DM on their toes.
This has had an interesting effect on my game. Originally I had envisioned the urban/home base aspect of the Fortress Eibon games, the outskirts of Yam City, to be the equivalent of the text menu interface of the old Wizardry computer RPG game: make new character; buy gear; sell gems; get unstoned; and the like.
Being a ham, I couldn't resist giving it atmosphere and character, but the explicit idea was that adventure took place in the dungeon.
However with the continued antics of the characters of the aforementioned players, and my desire to provide full agency to the players, hijinks have definitely ensued.
This has had me musing on quick resolution for such antics; I usually use d6 or a 2d6 reaction roll to adjudicate how they play out. I break down the probably outcomes and compare them to the roll result to see which way things play out.
Usually you could break down the outcomes of risky endeavors into four abstract outcomes: success; success with repercussions; failure; failure with repercussions.
For the determination of scam/heist activities, the DM makes a judgement on an adjustment, usually using a ability score modifier with further adjustment for the quality of player plans and preparations, and adjusts the results of a d12 roll by this integer, comparing the results to the table below, with the caveat that any roll that is a natural 1 is an automatic failure with repercussions.
10-12 - Success
9 - Failed Attempt *
8 - Success with repercussions
7 - Failed Attempt *
6 - Success with repercussions
5 - Failed Attempt *
4 - Success with repercussions
1-3 - Failure with repercussions
* on a result of Failed Attempt, the players may press their luck and continue their endeavor, making another roll as above but with a cumulative -1 modifier for each result of Failed Attempt *.
Repercussions are determined from what would be appropriate by the DM, with a further d6 roll used to determine the severity of the repercussions.
Example
Bill Snakehat is pretending to be a long lost distant relative of a wealthy family in order to claim an inheritance. The DM determines that: Bill Snakehat has a +1 charisma modifier; he has the signet ring of a long lost distant relative (+1); but his plan is preposterous (-3), for a net modifier of -1.
Bill Snakehat's player rolls a d12 and gets a modified result of 5: Failed Attempt. The family does not believe Bill Snakehat's claim. Bill's player attempts to press his luck and arranges for a crooked lawyer to produce fraudulent documentation to support his claim.
The DM makes the roll and gets a result of 7: Success with Repercussions. They than roll a d6 and gets a result of 6: The most severe of repercussions. Bill Snakehat receives the inheritance but a family member hires a gang of assassins to kill him.
"While it could be argued that Zodar's following (SaSS) expedition was a worse adventure than this, as it cost the party something close to 20,000gp, several magical items, and, with that second ambush, possibly the lives and/or sanities of a handsome dwarf and an experienced fighting-man, it should also be noted that before being ambushed the first time, they managed to level up a total of three characters. When compared to the total losses/loot, one must concede that this was truly the worst adventure ever.
Featuring:
Belbarrick and Zodar Khan, clerics of Orderon.
Kalikarr, cleric of the Church of Law.
Ranndy Serpenthelm.
Mern the Blue.
Murg Serpenthelm the slaver.
Summary
Balbarrick and Zodar Khan enlist Mern the Blue and somebody who claims to be Bonspiel but is probably Ranndy Serpenthelm, but Balbarrick is destroyed by explosive mushrooms, and Mern is slaughtered by evil cultists. When Zodar and Ranndy replace Belbarrick with another Lawful cleric and Mern with another Serpenthelm, a second foray into Fortress Eibon goes even worse and a small army of slaves are immolated. Zodar and Ranndy leave, dejected.
Two Worlds Collided and They Could Never, Never Tear Us Apart
Balbarrick and Zodar Khan are a couple of lawful clerics, new in town and eager to brave the terrible chaotic blight that is Fortress Eibon. Floria the Viperhearted sends them to some of her fellow adventurers, and unfortunately for them they run into crafty ol' Ranndy Serpenthelm who seems to be masquerading as a cleric named Bonspiel. Since he's not even a lawful cleric, Balbarrick and Zodar take no notice. This "Bonspiel" is also accompanied by Mern the Blue, a wizard of some repute.
Trying to Find Heramphalmos
Ranndy has nothing but disdain for the mercenaries, who hold him in equal if not more contempt. A young kid and an older stalwart determined to look out for him decide to accompany the party. He also buys a slave and sends Balbarrick to look for Heramphalmos. The doughty cleric follows a convoluted trail that leads to Jezehell, his wife, who is a whore at a place called Bitches with Whips, on Whip Street. Balbarrick gets nothing he can use from her, so Mern the blue goes down to harrass her. He tries casting Charm on her, but the other whores realize and forcibly detain her, while threatening Mern as well. He leaves frustrated.
Into the Fortress
The four heroes go to the Locust Courtyard and check out the lone door. Some men trying to catch locusts there tell them it's the door to the thieves' clubhouse. The party enters, and finds a room full of mushrooms. Balbarrick and one of the slaves touch a mushroom and are immediately immolated in a flash of light. Ranndy Serpenthelm uses his ring of telekinesis to move Balbarrick's body all over the room and explode all the other mushrooms. A little piece of Zodar Khan's faith in the goodness of law and order dies.
All That for Nuthin, Damn
Below the thieves' clubhouse, they find some caverns and a chaotic cult. Ranndy asks for the priest, and he shows up. Unable to get free stuff reach a compromise, the party attacks. Mern and the young mercenary are killed by the cult's fighters, but their reinforcements are blocked by Zodar Khan's flaming oil. However, when things seem to be going badly for them, Zodar and Ranndy look at each other and, in an instant, reach a decision. They flee for their lives, leaving the older mercenary to fend for himself. When he decides not to follow them, Zodar blocks their exit with flaming oil, and they return to the camps outside Yam.
Slave Drivers
Instead of more mercenaries, Ranndy decides to buy slaves, and recruits yet another of his many cousins. Zodar Khan recruits yet another foolhardy cleric of law, Kalikarr, and the lot of them return to Fortress Eibon. They decide to go up through the killing floor in the main entrance, but as soon as they send two slaves up there, they cut the rope and flee! Ranndy uses his ring of telekinesis to drag one of them back, and then punishes the other slaves for his betrayal.
Finally, Some Action!
The party goes up into one of the towers, but sadly runs into some sort of dragon-like spider creature, which breathes fire at them, immolating all their slaves at once. Ranndy is paralysed, but uses his ring of telekinesis to float away from the fight while Zodar Khan watches his back. The rest of the party is killed.
Accidental XP and a Final Note
On the way out, the escaped slave ambushes the duo and is killed."
By Johnstone of Red Box Vancouver