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Context: A sandbox campaign with players having a stable of characters. One character of one player is kleptomaniac (has the envy drawback), which requires them to steal 10 gp (a large amount of cash) each day or suffer penalties.

How can I handle the pickpocketing so that it only takes a small amount of real life time (unless there is trouble) and has plausible potential for profit, as well as significant risk of consequences, as any attempt to earn obscene amounts of cash by thievery should have?

I want the resolution to be fast when everything goes smoothly, but we can zoom in and play the event out in detail when there is trouble of adventurous kind.

Since this is a sandbox setting, the rules solution should not depend on the level of the character in question, in the sense that the world should not twist to create level-appropriate challenges or level-appropriate rewards. Any character should be capable of engaging the relevant rules system, and if it turns out that someone focused around sleight of hand can get rich this way, then so be it. That is: The outcome should depend on how skilled the character is, but the game master should be capable of engaging the rules system without ever knowing the level of the character.

I am running the game in a (GDS/threefold) simulationist way, so my first priority is in what makes sense in the context of the setting. Glossing over potential challenges is not acceptable, since the characters facing and trying to overcome challenges is the purpose of play (an instance of gamist creative agenda, for those conversant in that particular theory).

In particular, we want the process of play to answer the following question: Can this particular character, under these particular circumstances, accomplish a particular goal? Is the player skilled enough to pull it off?

To answer this, we need a procedure that respects the fictional reality and glosses over parts that are tedious or repetitive to play through.

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  • \$\begingroup\$ How is it decided which PCs from the stable get to participate each session? Is each player's stable deep enough to have another PC with aims and priorities similar to thief's? \$\endgroup\$ – Hey I Can Chan May 2 '17 at 17:39
  • \$\begingroup\$ Further, how are you handling demographics? That is, is there a central town (that you've mapped and populated) where adventures begin and end or is it classic scattered settlements of no particular interest in the middle of nowhere except that they're near enough to a dungeon to allow PCs to resupply? \$\endgroup\$ – Hey I Can Chan May 2 '17 at 17:47
  • \$\begingroup\$ If something is going on from previous session, then we play that with the involved characters. If not, players decide among themselves what they are going to do and who are involved. If a player is not in, then we try to play things where their characters are not involved, or can be handwaved away. Currently the thief is the only one with such interests. \$\endgroup\$ – Tommi May 3 '17 at 5:05
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You seem to have the following goals:

  1. quick resolution
  2. plausible profit potential
  3. meaningful risk
  4. sandbox-friendly
  5. non-leveled

I submit that these goals are mutually exclusive, as a set.

The biggest problem is the quick resolution goal vs. the meaningful risk goal: in the failure state of the theft attempt, meaningful risk (eg., a chase scene, jail time, etc.) will tend to take a lot of table-time. Depending on the player, even the success state could take quite a bit of time, as they narrate how they try to get situational bonuses to their check.

Further worsening this tension is the sandbox situation, which typically (in my experience) means that the PCs have a base in/near a specific point of civilization (a city, a village, etc.); the citizens are going to notice a rash of high-value thefts and will start to go on the defensive (potentially hiring the very PC who is stealing from them!).

Quick resolution plus a plausible profit potential also raises a red flag: why would the PC spend time adventuring (and risking life and limb) when they can just keep picking pockets and live a much safer (though, potentially, slightly less comfortable) life?

Rather, I submit that the player has chosen a character option which is inappropriate for the campaign you want to run: the player has chosen an option which requires spending precious table time focused on their repeated attempt to do the exact same thing every day, and an activity in which the other players are unlikely to be engaged, and which is likely to cause them grief. ... triply so since the character in question might not otherwise feature in the session. This isn't something that can be handwaved easily, unlike a requirement that the character spend an hour a day in quiet contemplation, or that they not eat meat (the latter of which could provide some interesting role-play situations, on occasion, but needn't come up every session). This is doubly true if the campaign doesn't revolve around dungeon delving or adventuring in the traditional sense for Pathfinder.

If the player truly wants to keep this mechanical facet of their character, I might suggest modifying the drawback such that a significant haul can sate the envy for a period of time, by granting a bonus on the Will save to avoid the penalties.

Without having playtested this, my first suggestion is that every 10% of their current wealth (defined as the purchase price of the non-consumable stuff they have on their character sheet (so, including armor, weapons, rings, etc., but not including potions, scrolls, or gems specifically carried for use as costly material components)) that they take without the explicit permission of the owner (which would include their share of loot from adventuring), they gain a cumulative +1 bonus on their Envy check until they fail an Envy save (probably to a max of +5). So, if a character with a +1 club (2300 gp) and no other gear gets 230 gp from a day of adventuring, get +1 to their Envy saves until they fail one; hauling out 460 gp the next day (not having to make a save, since they stole more than 10 gp from that grave), they'll get a +3 on their Envy checks until they fail one.

Further, I would encourage the player to role-play their Envy in line with that sating mechanic. Instead of "just" going out and pick-pocketing 10gp worth of stuff every day, they go through cycles of "at last, I have enough" -> "well, I'm doing okay" -> "he's got something shinier than I do, but civility says I shouldn't take it" -> <takes it>.

Off-screen, then, the PC is inventorying their newest acquisitions, showing them off to the fashionable set, etc., while working off their bonus until their time to be on-screen comes back around.

This modification doesn't give you all 5 goals, but I think that it hits 1, 4, and 5 well, and leaves 2 and 3 for when the character is already in the spotlight.

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  • \$\begingroup\$ The situation need not be handled fast when there is adventurous trouble, but we do want to get to that trouble fast. \$\endgroup\$ – Tommi May 2 '17 at 4:17
  • \$\begingroup\$ I assert that Envy is designed to cause adventurous trouble on a routine basis. As a drawback it should have drawbacks; but, I submit that its drawback affects the other players far more than it affects the character. If your primary goal is to quickly determine whether tonight's session will revolve round Envy, simply choose - the character's envy is sated enough for now, they feel the need to run a heist, or the guards are coming for them (to catch the new thief running amok in town?). Use the hook instead of submitting the other players to Yet Another Envy Check every session. \$\endgroup\$ – minnmass May 2 '17 at 14:17
  • \$\begingroup\$ On what principled ground can I make the choice between heist/envy/penalty, given the sandbox style of play? I'd prefer to keep the drawback as written to the extent that it is possible. \$\endgroup\$ – Tommi May 2 '17 at 14:36
  • \$\begingroup\$ @Thanuir: simple: role-play the town and the drawback. Is the Envious character taking opportunities to pilfer valuable stuff? Envy sits back and enjoys the show. Are they really bad at it? The guards come to arrest them. Are they exceptionally sneaky and skilled? the guards come to hire the adventurers. Is the character ignoring Envy other than the odd pro-forma mention? Rule-Zero that the centerpiece of the museum's new exhibit has caught their eye or decide that the tax collector is coming through town. Don't let "sandbox" mean you cede all control over the world. \$\endgroup\$ – minnmass May 2 '17 at 18:45
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    \$\begingroup\$ "Are they really bad at it? The guards come to arrest them. Are they exceptionally sneaky and skilled? the guards come to hire the adventurers." This is what the rules should determine. (The point of sandbox play is cede as much control as possible.) \$\endgroup\$ – Tommi May 3 '17 at 4:28
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A drawback is not an advantage. You should not profit simply for being a kleptomaniac. You are looking at things different from the developer's intent.

If it was simple to obtain 10 gp a day, it wouldnt be a drawback. And if the intent was to be a minor incovenience, it would be a small sum, like 1 gp, instead of an unrealistic value (for commoneers) like 10 gp. Remember that not all kleptomaniacs will be adventurers, and when trying to obtain their fix, they will likely get intro trouble.

Profession and downtime

If we look at the average profit from honest workers, like from the profession skill or using the downtime system, the character is looking at 1 or 2 gp a day of work. A character would need a +90 modifier on his profession skill to earn 10 gp a day using the downtime system for example. It's not impossible, but he would have to be the owner of sereval successful business to pull that off.

So, don't expect a buglar to obtain 10 gp a day casually, because he won't. The point of the drawback is to be an issue to the character. The klepto would need to pull several sucessfull crimes, like robbing the owner of several sucessfull business, in order to keep his drawback controlled.

If you, or the player, are not okay with that, consider replacing the drawback. Because you can totally be an addicted to pickpocketing without any drawbacks, but instead of robbing 10 gp a day, you are satisfied with 1-2 gp.

Or, instead of trying to obtain 10 gp a day, you could say that the character attempts a robbery every week and obtain the average of a week of work. At +10 skill bonus, that would mean 10 gp a week using the profession skill and taking-10 on your check. Instead of pickpocketing every day, he plans a new heist every week. He will suffer the penalties for a few days, but once he makes his skill check, those are reset to zero.

Heists

Finally, the last option is to plan a Heist. The heist does not need to be complex, or require all the player characters to participate, but must have a clear goal and the character has to do some legwork (knowledge/diplomacy checks) to figure out the location, security, logistics, etc. This will require a lot more work from the GM, as he will need to define what is available to be stolen, from whom, where, when the character can do it, and what kind of difficult he will face on his lone quest. But the heist rules will offer plenty of ideas so you both can work on it without much difficulty.

The Black Markets Player Companion book actually gives a example of simple heist that the GM can apply on this kind of situation:

  • Heist:

One or more of your loyal teams infiltrate (see below) an organization or property to steal valuables or information.

You must spend 1 day of downtime and succeed at an Appraise or Sense Motive check (DC = 20 + settlement or black market’s Law modifier) to assemble the ideal recruits and provide them the necessary information on their target.

At any point in the next week, your assembled team or teams can perform their heist, attempting a check to earn capital as if performing skilled work. Because this capital is stolen from another organization, you do not need to pay the associated gp cost for earning capital. Assembled teams must succeed at a DC 20 check to earn capital, or else they fail and are reported or broken up.

Performing a heist to generate Magic capital imposes a –5 penalty on this check.

Regardless of the result, your target suspects your involvement. Blame can be deflected with a successful Bluff check, which may benefit from an alibi (above) or manipulating evidence.

To perform a heist without arousing too much suspicion, your team must first infiltrate it (see below).

The bolded part talks about earning capital, which is explained on the downtime rules. But basically you can earn something worth at least 20 gp using these heist mechanics. Which should be enough to please our kleptomaniac.

  • Infiltration:

You spend 1 day of downtime to insert one of your teams into another organization to feed you information or steal resources. Doing so requires a successful Disguise or Bluff check against a DC of 20, modified by the settlement or black market’s Crime (for criminal organizations), Law (for law enforcement and military organizations), or Society (for governments and businesses) modifier.

While infiltrating another organization, your team can attempt checks to earn capital on your behalf, using any non-team bonuses provided by the infiltrated organization’s facilities and resources; you must still pay any associated cost for earning capital. Alternatively, your team can spend 1 day of downtime to attempt a check to earn capital and treat the result as a Diplomacy check to gather information regarding the organization, reporting the discoveries to you.

An infiltrating team remains ensconced for 1 week, plus 1 week if you succeeded at your initial check by 5 or more. You can perform the infiltrate activity up to once per week to maintain a team’s infiltration for extended periods. An infiltrating team can perform no other downtime activities on your behalf.

Instead of earning capital or gathering information, an infiltrating team can spend 1 day to perform a heist (see above). This ends the infiltration, but deflects any suspicion away from you or your organization; the target of the heist must succeed at a DC 20 Perception check (modified by the earning bonus your team used) to find any evidence of your involvement. Targets that fail their Perception checks by 5 or more don’t realize they were robbed.

A team of robbers should have an initial cost of about 200 gp to hire, train them, and earn their trust. But after that, they provide a +4 bonus on capital checks to earn money, goods or influence. A week of regular work (assuming you have no other bonuses on your capital check) should earn about 5-10 gp. This is not enough to fix the drawback, so the character will need to plan those heists regularly.

Settlement modifiers

Regardless of the chosen option, remember that the Settlement might have modifiers to the character's check, such as Crime and Law rating, which both affect pick picketing attempts and the security of the town in the form of guards and ease of robbery. The Economy modifier can be applied to profession checks to earn money, legally or not. The Society modifier can help the character on his disguise checks to infiltrate places. And the Lore modifier can be applied to all knowledge checks to research information and diplomacy checks to gather information. If everything fails, the Corruption modifier can help you bluff your way out of guards.

Character's reputation

You are also able to track the character's reputation within that settlement. Depending on what types of crimes he pulls off, this might earn a bad reputation with the city guards, but a good reputation with the crime organizations (such as the local thieves's guild).

To make it simple, you have 4 options:

  • Have enough Profession (Pickpocket) (or another relevant profession) to earn 10 gp a day, or +90 to be able to take 10.
  • Own several crime business that together can earn 10 gp a day, or +90 on the capital check to earn money.
  • Take the penalties for several days, but pull a robbery per week. That way the penalties are gone for a day and will start increasing again while you adventure (but hey, you can rob your friends and reset it again).
  • Plan a heist, which will take more time from the GM to plan the details so the character(s) can follow through their crime.
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    \$\begingroup\$ The economic scale of the thievery that's at the core of this really is staggering. If Pathfinder commoners earn what 3.5e commoners earn—an average of 2 sp per day—that means robbing fifty commoners per day. That's not a mere kleptomaniac but a one-man daily crime spree! \$\endgroup\$ – Hey I Can Chan May 1 '17 at 19:01
  • \$\begingroup\$ @Thanuir Why rob the bad guys when the other PCs are right there? ;-) \$\endgroup\$ – Hey I Can Chan May 2 '17 at 9:23
  • \$\begingroup\$ " This does not allow us to determine what happens in play as the character makes the attempt." - If you do not tell us the details, how are we supposed to know? What is he attempting? What are the risks? Are there guards? How many? How well armed? What type of doors and safes/chests are there? Are there guard dogs? Magical alarms? Ghosts wandering the hallways? The rules cannot guess this kind of details, it can only show you how to apply these details, the GM decides which ones apply or not to a given situation. \$\endgroup\$ – ShadowKras May 3 '17 at 12:30
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Most of the time you can handle it during the session.

So the characters are adventuring and they go down in the dungeon, and they find loot -- right? So the character takes some of the loot. That's probably worth 10gp right there.

The characters are in the wilderness and they fight some kobolds. The kobolds have crossbows; the player takes one of their crossbows. That crossbow was worth 35gp. It's your call whether it counts as "stealing" if the player takes it off the kobold's dead body, but I'd recommend you allow it. That kobold may not have a Last Will And Testament written out, but he probably has some friends somewhere who would have inherited his crossbow if you hadn't taken it.

Basically if there's any combat at all, there's going to be enough loot from the combat that the player can "steal" 10gp and not have to deal with the drawback for the day.

(And, if there's no combat, the character could choose to just not steal anything and deal with the penalty. It's not like the penalty would matter, except for the very first combat after a stretch of downtime.)


But what if the player just wants the character to steal things?

Your player's choice of trait suggests that he's interested in doing one-on-one heist scenes with you as the DM.

Most of the time, when someone wants to do a one-on-one scene with the DM, we say something like: "that's not interesting to me since it doesn't advance the plot, let's handwave it" or "I'd rather not put the rest of the players on hold, so if you want to run a one-on-one scene let's arrange a separate time when it's just the two of us at the table."

But you've indicated that you're running a simulationist game, so the above answers don't work for you.

You've asked us to homebrew you a skill challenge that will substitute for a heist. I don't think that's going to work, because the stakes are too high.


You need to simulate the stakes properly.

The reason stealing is a problem for most DMs is that the penalty is so bad if you lose: once the guards know your name and face, you can't be in that town any more. If you as the DM had plot in the town, a failure on a stealing check has just killed that plot, at least for that character. This is really rough for many campaigns.

But you're running a simulationist game, and the players have a stable of characters anyway, so I recommend that you embrace it. Make it clear to the player: "If you fail a check badly enough, your character becomes an outlaw. Your character might get killed, have to leave town, and/or become an NPC."

You will also need to handle the reactions of the other characters with grace. Most of the time the DM says something like: "well, your characters all have to be in the same adventuring party because otherwise we can't play the game. So everyone needs to think of reasons why you're all in the same party." If one of the characters just got caught committing grand theft, that's not going to work as well. You'll need to be prepared to turn to the other players and say: "Your buddy Bob just got caught committing a crime, and he's left town. Are you going to follow him into exile? Or is he on his own, and you'll find someone else who's not a crook to hang out with?"

Because the stakes are this high, you can't just use a skill challenge -- you have to actually play the scene out.


Stealing from the town should escalate in difficulty.

You can't pickpocket gold pieces off of anyone (except for adventurers). People don't carry that kind of money around in their pockets. If you want to steal that much money, you need to break in to somewhere.

The character's first few thefts will be pretty easy. After that, anyone with any money is going to hire guards to protect their stuff. Each theft will involve multiple checks: investigation to find a place to steal from, disable device to break in, investigation again to find where the valuables are hidden, stealth to avoid drawing notice. I recommend drawing up a list of people in town who have money, and their particular household defenses: rich merchant, mayor, guard captain, village witch, village wizard, village priest. If you have the scene prepared in advance, it will consume less game time.


Finally: consider just telling the player not to do heist scenes.

When the players are attempting to take the game in a direction that's not fun, there are two general paths the DM can take. The first is to let them do it, and let them not have fun, and then tell them: "it's your fault you didn't have fun, because you did this thing you shouldn't have done." The second path is to just tell them they can't do the thing because it wouldn't be fun.

It's not clear to me whether these heist scenes, with the attendant likelihood of losing the character, would be fun -- for you, for the player, or for the other players in the group. If you really don't think they would be fun, you should really consider just saying no.

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  • \$\begingroup\$ A good answer; thanks. I think the player determined the drawback randomly, so inferring exceptional motivation towards heists is probably not justified. I guess the play is okay with a brutal sandbox and consequences for their characters. \$\endgroup\$ – Tommi May 4 '17 at 4:56
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A first draft of a ruling; not playtested yet.

Knowledge (local) for finding good hunting grounds

DC 10 check allows the pickpocketing roll to be rolled with no penalty, DC 15 gives +2, DC 20 +4, etc. on the roll. Beating DC 5 gives a -5 penalty. A smaller result indicates an ambush (by city guards, previous mark or other thieves).

If you don't look for new hunting grounds after each pickpocketing roll, you suffer a cumulative -1 modifier on the pickpocketing roll.

The roll to find new hunting grounds suffers a cumulative -1 modifier for each previous change of hunting grounds. This penalty decays by 1 for each week without new pickpocketing by the same character. A disguise check, DC 10 + the cumulative penalty (consider the penalty to be a positive number when calculating this DC), negates the modifier on the knowledge (local) check.

The difficult of the knowledge (local) check and the rate at which the penalty increases should be adjusted depending on settlement size.

Locating and moving to new hunting grounds takes an hour.

Sleight of hand for picking pockets

DC 10 result gives d6 copper coins, DC 15 result d6 silver coins, DC 20 result d6 gold coins, each 5 beyond that increase the haul by d6 gold coins. A result of 5 implies there is no trouble, but no reward, either. Less than that and the thief is observed red-handed.

Each attempt takes d\$ 6\times 10\$ minutes.

Analysis

Consider three thieves; a rookie with +0 modifiers, a professional thief with +5 modifiers and a master thief with +10 modifiers.

The rookie is reasonably likely (around 2/5 chance) to get into trouble on their first attempt and the odds only grow worse. They do have a fair chance of earning a few coppers or even silvers, but repeated attempts lead to doom. 10 gold pieces a day is utterly hopeless.

The professional has around 1/100 chance of getting into trouble on the first attempt, with the probability increasing slowly. Especially if they use disguises, there is a fair chance that they can keep the business going for some time. Eyeballing, they have a fair chance of earning plenty of silver (amounting to some gold) on their first night, but 10 gold seems out of reach. Repeated attempts will lead to certain trouble.

The master can make around 30 pickpocketing attempts with no risk, so they should be capable of keeping up their 10 gp a day lifestyle for longer than half a week without risk, and for longer with modest risk.

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  • \$\begingroup\$ @AnneAunyme thealexandrian.net/wordpress/587/roleplaying-games/… \$\endgroup\$ – Tommi May 2 '17 at 9:00
  • \$\begingroup\$ @Thanuir After reading your link I figured what bothers me with calling someone with +10 a "master" and someone with +5 a "professional". In Pathfinder assuming you are a human with 12 in Int (that's not even hard) and a class with 4 ranks by level (that's not much), and take the favored class bonus, it means you get 7 skill ranks by level. It means that at lvl 1 you can easily have something like +5 in 7 different skills. Do you know people that are professionals in 7 different fields? I don't, but considering your scale it should be common. \$\endgroup\$ – Anne Aunyme May 2 '17 at 12:18
  • \$\begingroup\$ @AnneAunyme +5 allows you take 10 with a result of 15. So you can routinely craft high-quality items. With +10 you can routinely craft masterwork items. Answering complex questions about your profession is DC 15. But yes, Pathfinder has poor resolution at low skill levels. This discussion is now fairly tangential; I assume we understand each other sufficiently that you can try your hand at solving my problem, if you are so inclined. The session is tomorrow. \$\endgroup\$ – Tommi May 2 '17 at 12:44
  • \$\begingroup\$ Actually the level 1 human pickpocket from the npc codex has the following skills: Acrobatics +7, Appraise +5, Bluff +6, Disable Device +9, Disguise +8, Escape Artist +7, Knowledge (local) +5, Perception +3 (+4 to find traps), Sleight of Hand +12, Stealth +7 \$\endgroup\$ – ShadowKras May 3 '17 at 11:54
  • \$\begingroup\$ A level 1 rogue character without any optimization can obtain 1d6 gp a week without any risk of being captured. 1 rank in knowledge local will get you +4 on your check, if he has 12 wisdom, he can take-10 to obtain that +2 bonus on his sleight of hand. Then, if he has 16 dex (+3) and invests a skill point, that is +9 already. He simply needs a trait that adds the last +1 to routinelly beat that DC 20 check. A character with Envy will have issues, one without the drawback can live easily with 1d6 gp a week. If he makes 10 checks a week, that is 1d6 gp plus 5d6 sp plus 5d6 cp. \$\endgroup\$ – ShadowKras May 3 '17 at 12:36

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