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This may all have been answered while I was absent.
Let's take a gang of rather merry but vicious bandits led by our dear friend Bluddwolf, cheerfully robbing the hell out of people in their travels.
If BW issues a SAD to a merchant, does he go chaotic for killing them?
If BW does not issue a SAD to a traveler, does he go chaotic for killing them?
How far does a settlement's law reach? Claimed hexes with POI?
Are NPC traversed roads considered to have laws against killing people?
Will BW go chaotic for killing someone on the roads AND have a Marshall chasing him down?
Or will he just have a Marshall chasing him down with no hit to his alignment?
If I have a LN settlement, can BW wait just outside of my settlement hex to catch travelers?
Does he have to hang out all the way back towards uncontrolled hex territory?
What alignment shift would BW face for killing someone, in which scenarios?
Does he go evil for killing someone regardless of laws or not?
Is killing someone an inherently chaotic evil act?
Is it only chaotic if it's breaking a law?
What if I belonged to a LG settlement and go killing BW's friends in the wilderness, what kind of alignment hit would I be taking out there?
What if I had a contract on BW for killing someone, will I be going chaotic/evil for killing someone that has a contract on them?
If I have a contract with BW's less trustworthy cohorts and they break it, what kinds of penalty are they going to suffer?
If I'm good and go into an evil city, what risks am I taking and what impact is it going to have on those that act on it?

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Well, since I am a center piece in your questions (brims with pride) let me take a stab at this.
All attacks (robberies) , including SADs, are chaotic acts.
All killing is evil, regardless of who is killed or who is doing the killing.
There is no alignment impact for actions against sanctioned targets ( feud, faction, war, assassination, bounty hunting or refused SADs). * Note a refused SAD would still incur the chaotic shift at the beginning, but not the evil shift for the killing.
This is my understanding.
Also to my understanding, NPC guards will only attack active criminal / heinous flagged characters and perhaps characters with some degree of low reputation (number unknown). Alignment is unseen by all except the Gods or through means of Devine magic. So entering a settlement of the opposite alignment should not be an issue. Casting an alignment based skill may trigger a trespasser flag, but thus us an assumption on my part.