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Isn't chaos a little... anti-settlement, by nature?
Ants have no laws, they each do as they want...the trick is either brainwashing your subjects to "want" to follow your system, or as evolution has done for the ants, design the system so when everyone does as they want, progress ensues. Amusingly, this was exactly The Seventh Veil's initial design philosophy.
For the record, I think they have since become much more...traditionally Lawful.

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And that, friends, is why 'lawful' is a poor word for that aspect of alignment. It was originally inspired by Michael Moorcock's Elric novels, and has been a tradition in D&D for nearly 40 years, but the point was never about the actual laws of governance. The alignment 'lawful' is about discipline, precision, structure, organization, etc. If ants weren't basically mindless, they'd probably be lawful neutral.
If it were about mortal laws, then a paladin could never enter a sovereign nation in which the law requires certain evil actions. If he does evil, he loses his paladinhood, but if he does not do it (and therefore breaks the law) he loses his paladinhood. If it were that simple, Cheliax could instate a law banning paladins from their holdings, and from the moment one tried to come in anyway, he'd become a second-string fighter without many feats.
For the purposes of PFO, in which your behaviour is judged by a computer, the laws of settlements, keeping or breaking contracts, and other measurable things will shift your alignment in regards to order & chaos. You could otherwise behave randomly and the server probably won't be able to tell if there's a method behind the madness that's making you /dance on the steps of a temple to Iomedae wearing nothing but boots and a bowtie.

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Chaotic good settlements could work.
You basically need a bunch of people with common goals working together for the common good whilst trying to have as few rigid set rules as possible.
A flexible creative artistic community of people working together without a need for a leader or lots of rules is not impossible.

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Chaotic good settlements could work.
You basically need a bunch of people with common goals working together for the common good whilst trying to have as few rigid set rules as possible.
A flexible creative artistic community of people working together without a need for a leader or lots of rules is not impossible.
Sounds like a commune... and those work on a tribal scale, but tend to fall apart eventually without a strong external pressure. I guess PFO may be dangerous enough to keep them working together while overlooking the small differences that could otherwise blow up into a dramatic schism.

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Keign wrote:Isn't chaos a little... anti-settlement, by nature?Ants have no laws, they each do as they want...the trick is either brainwashing your subjects to "want" to follow your system, or as evolution has done for the ants, design the system so when everyone does as they want, progress ensues. Amusingly, this was exactly The Seventh Veil's initial design philosophy.
For the record, I think they have since become much more...traditionally Lawful.
THE ANT NEST: Ants have laws If you ain't a member of the nest you are an enemy (and thus executed)- and they are isolationist by nature. They also have a policy of expelling or killing the weakest Queen when multiple leaders arise. Breeding Control ensures that children are born workers, Warriors, Drones, And a Queen only when a Queen is needed.
I would say Lawful with Totalitarian-Isolationist Tendencies). From a Human perspective Lawful Evil.

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Chaotic good settlements could work.
You basically need a bunch of people with common goals working together for the common good whilst trying to have as few rigid set rules as possible.
A flexible creative artistic community of people working together without a need for a leader or lots of rules is not impossible.
Freeholders: Its hard to create a Model for this one. Consensus Government requires the consent of every member so no one is trespassed on. So you might have Freeholds (but because the family is a Lawful Patriarchy/matriarchy You might have individuals farming their own land). So People living apart. Children might be conceived in trade but Trade Rules are Lawful so it may not be imposed - merely what will you give in return?
Consensus Government is the Ideal Lawful Good - one that protects every one by requiring the consent of every one. Unlike Democracy there is no chance for Tyranny of the few governing the Many.

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A Chaotic settlement would follow a parliamentary system with multiple factions and sub-factions, with a Prime Minister who has the simple majority vote amongst possibly dozens of candidates.
Think of modern day Italy, which has had some 50 governments on 70 years. However, there is still a common defense and other unifying attributes in a government system such as this. A Chaotic settlement can still have laws, but in many cases they would be arbitrarily enforced and or punished. There would also be a fair amount of corruption, usually bribery and embezzlement.
The settlement would have many different neighborhoods, each with their own set of rules and governed by a neighborhood leader. These neighborhoods would be semi autonomous, but required to meet the few requirements set by the settlement as a whole.
As a Nuetral settlement it would still be open to both good and evil. It's Chaotic side would allow for some inconsistencies. For example, its special police force (not its military) could actually be Lawful Evil, distributing justice swiftly and very severely. I doubt the same could apply to a Lawful Good police force, the aspects of their alignment would make it very difficult for them to function in this settlement.
I still have a lot to think about. Setting up a community like this will take a lot of people coming together and meshing together all of these ideas.

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A rule of strength works well for for a chaotic group all thew the the leader my change a lot there only one way to be goblin king.

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Well a lot of this depends on the Game Structure vs the Out of Game structure. Remember the only thing that matters is reputation.
So I want to make a Chaotic Neutral Setlement? Make it with a group of CN fellows (players can farm to it then refuse positive bonuses). And form what is basically a nation of "stand and deliver" Bandits with little to no laws {IN GAME}.
Meanwhile out of the game you make rules and laws and that are agreed upon and punished (possibly with exile) if not followed. The good vs evil alignment can be touched up with PvE to maintain Neutral alignment. And its ok to have max Chaos alignment (hello, Chaotic settlement). And stand and deliver and a few other things can be done to keep reputation high.
Dont get me wrong, it seems a bit wierd to have this organized chaos. But this is what Bandits like myself woud need to do to have successful settlements, which would lead to top notch training for the criminal side, which would ultimately lead to personal success as a bandit.
TL;DR: You RP and use in game mechanics as Chaotic, In the back ground you are quite organized and structured.
I appreciate all the feedback, and it is an interesting topic to talk about. However this is way off topic, and if no one wants to talk about the Original Topic, then just let this thread die please.

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Remember there are degrees of Chaos. They can range from "Randomness" to outright "Anarchy".
A Chaotic Neutral settlement can have a law against murder and yet have dueling perfectly acceptable. I see that there would be only one true God in a CN settlement... The Gold Coin, and any transgression can be absolved through the use of the all mighty!
Prisons cost money, fines are free and increase revenue.

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KitNyx wrote:Keign wrote:Isn't chaos a little... anti-settlement, by nature?Ants have no laws, they each do as they want...the trick is either brainwashing your subjects to "want" to follow your system, or as evolution has done for the ants, design the system so when everyone does as they want, progress ensues. Amusingly, this was exactly The Seventh Veil's initial design philosophy.
For the record, I think they have since become much more...traditionally Lawful.
THE ANT NEST: Ants have laws If you ain't a member of the nest you are an enemy (and thus executed)- and they are isolationist by nature. They also have a policy of expelling or killing the weakest Queen when multiple leaders arise. Breeding Control ensures that children are born workers, Warriors, Drones, And a Queen only when a Queen is needed.
I would say Lawful with Totalitarian-Isolationist Tendencies). From a Human perspective Lawful Evil.
This is us projecting human culture on them...of which they have none. No ant is even aware of any other ant (they do not actually communicate explicitly nor do they actively coordinate), they each act as they are programmed to individually do (with a bit of randomness/chaos). These policies you speak of are nothing more than "emergent" properties of the overall system; order we project onto the system. Since each ant acts as it individually wills without regard to any external law or order, that sounds like pure chaos to me.
Maybe if you go far enough in any one extreme in alignment, one starts taking on the characteristics/behaviours of the opposing alignment.

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So, take the classic chaos illustration from Jurassic Park...because you know the drop of water will roll down-slope (off her hand) you think it is predictable and therefore not an illustration of chaos?
EDIT: Sorry, was trying to make a point...but I did not mean it to sound so snarky, so please do not take it that way.

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There will be quite a bit of meta game to this game. Also while the original people who play this might be more into the role playing aspect I am almost certain that people who come later will just want to play the game and will nto give two s$@@s about role playing their alignments. Thus there will be quite a few settlements for every alignment that function just fine due to the meta game "laws" (aka dont f%+! with your guild/alliance mates or will will kick you out)

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yellowdingo wrote:THE ANT NEST: Ants have laws If you ain't a member of the nest you are an enemy (and thus executed)- and they are isolationist by nature. They also have a policy of expelling or killing the weakest Queen when multiple leaders arise. Breeding Control ensures that children are born workers, Warriors, Drones, And a Queen only when a Queen is needed.
I would say Lawful with Totalitarian-Isolationist Tendencies). From a Human perspective Lawful Evil.
This is us projecting human culture on them...of which they have none. No ant is even aware of any other ant (they do not actually communicate explicitly nor do they actively coordinate), they each act as they are programmed to individually do (with a bit of randomness/chaos). These policies you speak of are nothing more than "emergent" properties of the overall system; order we project onto the system. Since each ant acts as it individually wills without regard to any external law or order, that sounds like pure chaos to me.
Maybe if you go far enough in any one extreme in alignment, one starts taking on the characteristics/behaviours of the opposing alignment.
Human behaviour is a load of emergent properties too, we're just more complex and flexible in how we form and change our societies.
In Golarion, ants are vermin and thus mindless and true neutral. They're not chaotic at all, but are highly structured and don't have any concept of individuality. They don't acts as they individually will because they have no individual will. They are effectively lawful but they aren't aligned that way since there is no choice involved.

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I'm actually curious which way I will lean with pocket ace at this point. My original intents were a LN Mercenary guild with a tendency to dabble in banditry. I always considered the lawful kind of crucial, because it's specific planning would be to follow through on whatever it agrees to.
IE in my mind when it comes to mercenaries, in lawful vs Chaotic, with the following scenerio.
Forces A and B are about to go to war, Mercenary company is offered 100k coin from force A, side B comes to them and offers 300k.
Chaotic option: Lead force A to believe you will fight for them, Then supprise them at the last second when it turns out you are actually helping side B. Greatly increasing side B's chance of success considering they did not get time to hire a different company.
Lawful Action: Once you have accepted an offer, no amount of money should override an already made deal.
Neutral action: Return to side A, inform them you have a better offer, grant them a chance to match it, if they decline, you fight for B, but they also aren't caught with their pants down in the way the chaotic option is.
Honestly the biggest thing I was kind of caught off guard though, S.A.D to me sounded more neutral than chaotic of an option. A lawful group could IMO consider a bridge theirs and charge a toll etc... though under current descriptions it sounds like being chaotic is the pre-req to... the less chaotic form of banditry... Something to which I have to wonder how mixed groups might work with the tags. IE I don't imagine solo banditry as a logical action, so what happens if a CE person with the outlaw flag, in a party with a bunch of lawful characters, and issues the stand and deliver. I certainly imagine an alignment hit of course, but what the extent will be interesting to learn.

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@ Onishi,
I was thinking the same as you about banditry and chaos and my original plan was to have The UnNamed Company run as a Lawful Neutral company. I was under the belief that if we stood by our contracts, that was a lawful trait. If we had rules against griefing, that too was a lawful trait. But, then I was corrected in my rigid interpretation, and I adopted this rationale:
There can be degrees of chaos, from simple "randomness" to "anarchy". If you imagine how many rules and laws, along with social morays and ethical questions, there could be thousands of "lawful" decisions to be followed. So, if we only follow a handful, that is still pretty darn chaotic.
Your scenario above paints the chaotic bandit as not seeing the bad business sense in double crossing a contract. That is not chaos, it is stupid, and will cost the bandit vast amounts of potential business in the future.
Instead I would consider the chaotic nature of my company to mean that we do not adhere to most rule or laws of others, but our own rules are an expression of our freedom. I view our Chaotic Neutral as a means to take any job from anyone, our only motivation is greed. However our greed is tempered by the patience that comes with knowing that greater wealth can be achieved by being intelligently greedy.

Valandur |

Something to which I have to wonder how mixed groups might work with the tags. IE I don't imagine solo banditry as a logical action, so what happens if a CE person with the outlaw flag, in a party with a bunch of lawful characters, and issues the stand and deliver. I certainly imagine an alignment hit of course, but what the extent will be interesting to learn.
Check this part of the video FAQ, it might apply to what your talking about...
Kaesh831: So, will alignment restrict my ability to play with other people in the world?
Stephen Cheney: So, Lawful Good and Chaotic Evil characters - there's nothing stopping you from being in the same party. You won't be able to join into the same official group because those are usually restricted to one alignment step. It's possible you could both be a member of a kingdom by a transitive property, but that'd be really hard to do, and I'm actually not sure how you'd do it. But you can be in the same party.
And, the important thing about that is that you would be really poorly off if you're the Lawful Good guy, because the Chaotic Evil guy has many less restrictions on his behavior than you, so he could embroil you in fights that cause you to lose alignment. Conversely, however, if you're running around and there are a bunch of Lawful Good knights running around that you've got your alliance rating with really high for them, the Chaotic Evil guy might get attacked by them and you wouldn't be. And vice versa for his factions that he's got on his Chaotic Evil character. So, that could wind up ruining the alliances you have, or you could just stand there and watch your buddy get beat up because you don't want to ruin your alliance.
I might be wrong in thinking this, but does this mean that one party members actions might not effect the other party members if they didn't take action as well? It almost seems to imply this to be the case, but I'm just not sure

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I might be wrong in thinking this, but does this mean that one party members actions might not effect the other party members if they didn't take action as well? It almost seems to imply this to be the case, but I'm just not sure
I took at as meaning that if you party with the wrong people you could be put in situations where they start fights and the game allows you to attack someone without penalty BUT if you do support your "party members" there will be political repercussions.

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There will be quite a bit of meta game to this game. Also while the original people who play this might be more into the role playing aspect I am almost certain that people who come later will just want to play the game and will nto give two s@$%s about role playing their alignments. Thus there will be quite a few settlements for every alignment that function just fine due to the meta game "laws" (aka dont f**@ with your guild/alliance mates or will will kick you out)
100% agree! Alignment is a game mechanic, and nothing more. You will play your character however you are going to play them, and their alignment will become whatever it becomes. Your choices will be your characters consequences, so alignment is a reflection of you moreso than how you attempt to role play your character. This is why the Devs have said you can lock or reject certain automatic shifts that occur over time. For instance, you can reject the shift to good or lawful if you desire that.
There is a bit too much concern over alignment in my opinion. This is a sand box MMO. It is not th PnP Pathfinder RPG. This game should focus exclusively on Reputation, again in my opinion. The skill system could be based on reputation, where a high rep is required to unlock certain skills, as well a low reputation being needed to unlock others.
Alignment, if needed couldn't be something that is locked in. So if you role a toon as a Lawful Good, you will remain lawful good, but your reputation may block you from having access to some of the skills. Best game example I can think of here is if you took dark side choices as a Jedi in Star Wars the Old Republic. You were still a Jedi but everyone could see the effects of the dark side on you, and you gradually became more restricted in using light side based equipment.
So here in PFO, could you claim to be a Paladin with a bad reputation? Of course you could, but that doesn't mean that other Paladins will accept you as one. How could a Paladin lose his powers? Through the lose of positive reputation.
The Devs have already said, reputation is more important than alignment. Then why not just have reputation as something we need to be mindful if then?
For those that say the Gods of Pathfinder have alignment, therefor we need to as well. The Gods have a focus and character types that tend to follow them, no need for alignment. A God of Thieves will remain a God of Thieves regardless if there is an alignment slapped on him/her or not.

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Focusing back on the idea of a Chaotic settlement..
I see the only viable option is to make this proposed settlement a Chaotic Neutral settlement at its core.
------- TN -------
CG----- CN -----CE
------- TN -------
The only alignment we need to avoid is Lawful. TN is not a problem because they will not shift the C vs. L or the G vs. E in any direction.
The purpose of making CN the center is that we would want this settlement to have the highest possible training opportunities for both Chaotic based skills and those that are Non Alignment specific.
Although this settlement may not have "etched in stone" laws, it could still have a number of guidelines and general agreements.
It would make for an excellent trade hub, out in the less secure wilderness areas of the River Kingdoms.
It would likely be inhabited by the more "free spirited" people of the River Kingdoms. A haven for Bandits, Barbarians, Rangers, Assassins, Merchants, Druids and all others that are not tied to the Lawful spectrum of the alignment system.
However, as a "free settlement" no alignemnt would be barred from visiting it either.
The only "activities" that would be banned within settlement hexes (limits) would be those of a Lawful nature. Some examples: Bounties can not be issued from or collected within settlement limits; A Cleric of Lawful Good or Evil would be prohibited from starting a congregation; etc...
The setting in the wilderness should be obvious. Most of the "classes" that I would think would be attracked to this settlement are those that we widely associate with the "wilderness".

Kobold Catgirl |

So, take the classic chaos illustration from Jurassic Park...because you know the drop of water will roll down-slope (off her hand) you think it is predictable and therefore not an illustration of chaos?
EDIT: Sorry, was trying to make a point...but I did not mean it to sound so snarky, so please do not take it that way.
No offense taken. If that drop of water has a mind and repeatedly chooses the same route, then yeah, I'd say it's lawful.

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As far as Chaotic settlements, I would think that most fantasy barbarian communes would fall under this by right of the 'might makes right' rule of accession they often have.
The Devs have already said, reputation is more important than alignment. Then why not just have reputation as something we need to be mindful if then?
I like the idea in principle. My understanding of reputation is that it tends to reflect your actions as a player and not necessarily your actions as a character (i.e. griefers lose reputation, well-RPed evil characters would gain reputation). So Im just wondering how that would work with an Anti-Paladin with a friendly player. Gains reputation for being a good player and suddenly loses his Anti-Paladin powers.
I think the real issue is the strict definition of good and evil actions in game, particularly the current 'thou shall not kill another player' rule of good. I really dont like that one as I feel it is excessively restrictive on good players (e.g. hunting bounties as a good character). Even when looking at different moral codes (such as the Knight from 3.5) the restrictions are usually on killing helpless/incapacitated foes, not foes that can defend themselves.
This problem is exacerbated by not having (to my knowledge) any nonlethal way of incapacitating/apprehending players. Having that might alleviate some of the problem, but without one the rule becomes very limiting.

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I think the real issue is the strict definition of good and evil actions in game, particularly the current 'thou shall not kill another player' rule of good. I really dont like that one as I feel it is excessively restrictive on good players (e.g. hunting bounties as a good character). Even when looking at different moral codes (such as the Knight from 3.5) the restrictions are usually on killing helpless/incapacitated foes, not foes that can defend themselves.This problem is exacerbated by not having (to my knowledge) any nonlethal way of incapacitating/apprehending players. Having that might alleviate some of the problem, but without one the rule becomes very limiting.
Well the crusader flag certainly seems to help with this issue, Evil characters of any sort become free game.
Champion (Good)
Champion is for players who want to proactively take the fight to the forces of evil. It allows players to more easily engage evil characters and earn reputation. As long as you limit your kills to evil characters, you get increasing benefits, but killing neutral or good characters ends your benefits; you still can suffer reputation and law vs. chaos loss for attacking evil
Though admittedly does not protect in the law/chaos axis, nor reputation.
and of course the existence of flags as a whole creating exceptions for everyone. Bounties are certainly a huge rope in things.
I do agree that the issue is at a high risk of problems, but I disagree on an incapacitation system being a good route to aleviate the issue. (as I've mentioned on the topics about such, so far there's been no proposed incapacitation system that isn't between 80% and 125% as bad as death, at which point it is better to make killing less bad, rather than implement a scenario nearly as bad or potentially worse for the victim, but give it a new name to undermine "killing")

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I'm bumping this to gauge any new interest in creating a Chaotic Neutral settlement.
Focusing back on the idea of a Chaotic settlement..
I see the only viable option is to make this proposed settlement a Chaotic Neutral settlement at its core.
------- TN -------
CG----- CN -----CE
------- TN -------The only alignment we need to avoid is Lawful. TN is not a problem because they will not shift the C vs. L or the G vs. E in any direction.
The purpose of making CN the center is that we would want this settlement to have the highest possible training opportunities for both Chaotic based skills and those that are Non Alignment specific.
Although this settlement may not have "etched in stone" laws, it could still have a number of guidelines and general agreements.
It would make for an excellent trade hub, out in the less secure wilderness areas of the River Kingdoms.
It would likely be inhabited by the more "free spirited" people of the River Kingdoms. A haven for Bandits, Barbarians, Rangers, Assassins, Merchants, Druids and all others that are not tied to the Lawful spectrum of the alignment system.
However, as a "free settlement" no alignemnt would be barred from visiting it either.
The only "activities" that would be banned within settlement hexes (limits) would be those of a Lawful nature. Some examples: Bounties can not be issued from or collected within settlement limits; A Cleric of Lawful Good or Evil would be prohibited from starting a congregation; etc...
The setting in the wilderness should be obvious. Most of the "classes" that I would think would be attracted to this settlement are those that we widely associate with the "wilderness".

Quandary |

The thread discussing arena combat make me envision a Chaotic Barbarian settlement/nation working such that any member who can defeat the leader in personal combat becomes their new leader. (ala Riddick/Necromongers) That seems pretty compatable with the CN settlement above... Although personally, I would be more partial to CG (still accepting of CN, in case anybody thought of messing with them). CE just results in too many enemies, and CN settlement (accepting CE) is basically the same just toned down a bit.
Each of the Settlement alignments really need a mechanical or game reason to choose them, otherwise Chaotic Barbarians can just join Neutral Settlements, and Neutral Barbarians can even join Lawful ones. This could be enhanced training benefits, but perhaps other benefits as well, group buffs that only work for members of Chaotic settlements, for example (which could be always on, or integrated with some class ability), enhanced resistance to certain types of Control effects, etc. (YOU CANNOT STOP THE HORDE!)
I don't see the higher upkeep costs of Chaotic settlements as a prohibitive distadvantage, it just means your raiders have to go out there and do their raiding (+Stand And Deliver, etc).
----------------------------------------------------------
Somebody, please give me the link to the Ant Paladin thread...

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I may be mistaken, but Barbarians are Chaotic and would not be just Neutral as you suggest.
I envision a Chaotic Neutral settelment:
-----TN-----
CG---CN---CE
-----TN-----
CN: Bandits, Barbarians, Druids (?), Clerics, Magic Usrs
TN: Any, but those requiring C or L
CG: Rangers, Bandits (Robin Hood types), Clerics, Magic Users
CE: Badits (who kill a lot), Assassins, Necromancers
These are just a few examples, I'm sure there are more.
This type of settlement would provide the highest level skill training the the alignment areas of Chaos and Neutral and a lesser degree in Good and Evil. Very little training if any in Lawful.

Quandary |

No, he's saying his CN /settlement/ may include, amongst the other PC alignments he listed (CG/CN/CE), some TN /PCs/.
Clearly, these TN /PCs/ may not be of classes which require C or L alignment (or Good or Evil),
but the (CG/CN/CE) PCs of the settlement /would/ qualify for classes which require C/G/E alignments.

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No, he's saying his CN /settlement/ may include, amongst the other PC alignments he listed (CG/CN/CE), some TN /PCs/.
Clearly, these TN /PCs/ may not be of classes which require C or L alignment (or Good or Evil),
but the (CG/CN/CE) PCs of the settlement /would/ qualify for classes which require C/G/E alignments.
Yes...
As I stated, my examples above were just the few I could think of. If CN is the center, then one stp removed in each direction includes: CG, TN, CE.
Classes that are tied to Chaotic and or Neutral will have the most training opportunity in this type of a settlement.
Classes needing Good or Evil will also find some training opportunity, but just not to maximum, I'm guessing.
Classes needing Lawful, would likely be SOL in this type of settlement.
This does not mean that lawfuls could not enter, they would just have limited skill training access. They would probably be restricted in some of their "Lawful" activities, like Bounty Hunting or building a church to a lawful Diety.
There may be laws against Lawful activities, which does strike me as being consistant with a Chaotic society.

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Chaotic good settlements could work.
You basically need a bunch of people with common goals working together for the common good whilst trying to have as few rigid set rules as possible.
A flexible creative artistic community of people working together without a need for a leader or lots of rules is not impossible.
Chaotic Evil can organize as well or there wouldn't be Demon Lords in The Abyss.
Chaotic Evil people like being in charge just as much as NE and LE (or LG, for that matter *cough*Andius*cough* ;) ). The difference is that CE characters have to be bullies. Well, more so than LE do. They have to rule through fear and pain to overcome the disobedient, unruly, backstabbing nature of their chaotic minions.

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Thornkeep, one of the three NPC starting settlements, is CN. For and example on how to build one, look there.
Thank You, for directing me to that. A few notes that we would have to consider if following that model.
First... If Thornkeep is in fcat a CN NPC starter town, then if would be a perfect location to spend the first few weeks or even months operating out of.
Now, ThornKeep is described as not having much of a defense, and in the game it wont need one, being an NPC town. But, any player settlement will not have that luxury.
There are several ways to defend a town, and remain Chaotic and Neutral.
1. Remain open to all, including Lawful visitors
2. Provide a needed service to all. Training in Chaotic and Neutral based skills is obvious, but making them very affordable even to outsiders maybe the key to safety.
3. Locate it where it can be an oasis of safety in an otherwise dangerous area. This will make it useful for all, as a weigh station and trade hub, deep in the wilderness.
With these three things, a settlement like this will be naturally defended by the "moat" of dangerous zones surrounding it. More importantly, its usefullness to everyone will be its best protection.

Kobold Catgirl |
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I think Riddleport is a good example of an easily-defended Chaotic Neutral city. Sure, it's a dangerous place and you're liable to get a knife in your back if you act like a moron, but pick a fight with the city as a whole and all those squabbling pirates suddenly come together to beat the stuffing out of you.

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Riddle port looks too organized, and I'm not even sure that is in the River a kingdoms, but as an example I appreciate the info.
I will wait to see what the Dev Blogs eventually say about settlement management and required leadership skills. I also want to see the response to the question, who is interested in such a project?
So far, from what I know, my company just maybe the only one dedicated to CN. I hope I'm wrong. But, if there are any CN player characters out there looking for a settlement, I hope they respond here.
I'm particularly interested in what clerics of CN Deities would be interested in setting up a church and gathering a congregation. I'm personally going with Besmara, but I'm not a cleric.