Why wouldn't Chartertopia dissolve into chaotic gang warfare?
This is the most common objection to any anarchy, and I believe true anarchy would end up with gangs and warlords fighting for domination, with or without property to squabble over. But my Chartertopia is not a true anarchy.
It does define a minimal government and redress.
Associations take up the slack for legates who want to be controlled or want to control others.
It breeds self-sufficient adults who don't take crap from legates.
I am not a complete idiot. If some genie were to wave a magic wand and convert the world to Chartertopia overnight, it would fail just as if it converted to a revival of the USSR or the Roman Empire. But I do believe that there are long term paths which could lead to something similar, and I believe that once people had been living in this society for five or ten years, they would be loathe to return to any kind of statist legacy.
Government as a figurehead
One of the purposes of government is to provide something for people to unite around; a flag, a name, slogans, and a national ethos — "No taxation without representation" or "Liberté, égalité, fraternité". I reckon the vast majority of citizens of any country know very little about what really distinguishes their government from others, as distinct to their culture or language. It's easy to know a country has a monarch or Prime Minister or President, but bureaucracies and politicians are the same the world over.
Chartertopia has associations, and you can choose what style of figurehead you want. No other government has that.
Chartertopia has slogans: Mind Your Own Business comes to mind.
Chartertopia certainly has a national ethos unlike any other -- self-control. It puts all the other claims of freedom to shame. Chartertopia will be at the top of every ranking of countries by freedom — except those which define freedom as the freedom of subjects to depend on their governments. But there again, Chartertopia associations will top the list.
Associations
Charter government by itself is about as weak a government as you can plausibly still call a government. That is why I believe people will form associations with like-minded friends and create their own governments under the weak Chartertopia brand.
Simplest of all have no special power. Insurance cooperatives, sporting clubs, family businesses, you name it, you can create an association to do anything, as long as their bylaws pass muster like all charter bylaws.
Guardian associations have more arbitrary authority. They can do anything to their members, because members have signed up as adults to become association wards, detailing all the rights they surrender, just as children are under the control of their parents. The difference is that because members sign up as adults, they can agree to be flogged for drinking or lose a hand for thievery.
If they don't want to handle their own investments, they can sign over as much property and income as they want to the association, and take whatever welfare, pensions, and insurance coverage the association feels fit to offer.
If they hate guns, pornography, immodest clothing, or other contraband, they can promise to never own any, and association bylaws can exact any punishment the association wants for violations.
If they don't hate drinking, smoking, dancing, swearing, or other taboos, they can authorize their association to pass all the restrictive bylaws they want, and fine and jail members for impure thoughts.
If they hate coddling criminals, the association can torture, shoot, or hang all members who commit whatever crimes the association has deemed suitable.
Why form associations instead of establishing a dictatorship?
They'd have to defeat every other gang fighting to be The One True Dictatorship.
They'd spend the rest of their lives fighting insurrection and conquest.
They'd have to compromise all too often with others in their power circle.
Imagine people who want everyone to tithe 10% of their income to any church. They don't even care what church; name it, send them your money. But you must give 10% of your income.
10% total, or do you exclude basic necessities such as housing and food?
What counts as basic necessities? Do you have to sell and move to a smaller house and buy smaller cars as your children move out? How often are you allowed to dine out, and where?
How do you know people are reporting all their income?
How many people would form their own church and tithe to themselves?
These tithers would spend the rest of their lives fighting all these battles, over and over, day after day, and never resolve the problems and squabbles.
Imagine instead they form a voluntary guardian association. The only right you surrender, aside from tithing, is that they get to monitor all your financials to make sure you are tithing, and the association maintains a list of approved churches.
Most tithing squabbles would be over which churches are acceptable.
Some would still squabble over basic necessities.
People who disagree are free to form their own association.
The only real literal fighting would be with a few fanatics who would never be happy unless they were in charge, most of whom would probably kill each other.
And last but not least, members of even the most vicious dictatorial associations always have the right to self-emancipate; to quit, even from the gallows. They may not get to take any property with them. They may lose their jobs. They may lose all contact with family and friends. But they will have their lives and the freedom to choose better next time. They can even choose to have no association.
The adults of the world
Charterites don't have to depend on government, even associations. Redress need not depend on associations, even redress where the other parties are members of other associations or not members at all; they just sign over that right to their association.
But I do not believe that most people would do this. Associations are third parties, and third parties do not have the primary parties' interest at stake. Suppose your association is trying to court favor with some other association, such as better trading terms or a merger. You have a contract dispute with a member of that other association. It's entirely likely that they will throw you under the bus instead of jeopardizing those negotiations.
I believe crime rates would drop by a factor of ten from having no contraband or taboos at the charter level. Associations may well have them, but that's an association problem.
One of the devils of modern society is so many government one-size-fits-nobody fixes to problems which were mostly created by previous government fixes. I call these devils because they stifle society for no reason, people resent being stifled, and they lash out, partly by siccing government on others before others sic government on them, but also by criminal acts. Minimum wage laws and occupational licensing have made it harder and harder for people to take care of themselves, and they resent depending on welfare and other government largesse.
Chartertopia has none of these. People may grow up in an association family and sign up when they become adults, but I suspect most would resent that suffocating coddling and strike out on their own. An insurance cooperative is a simple step and avoids those minor annoyances. An investment association also pays a small price for more avoided annoyances. Both can be switched at will, because these are not guardian associations. Members can also drop out and manage insurance and investments for themselves as they learn more.
All this choice breeds adults. Even if half of charterites are association members, the presence of so many non-members, and members of different associations, creates day to day awareness of all the possibilities. People probably aren't even aware of what associations, if any, their friends, neighbors, and co-workers belong to, any more than most people today are aware of what churches or grocery stores they go to. And when they learn that their neighbor of five years or new co-workers belongs to a guardian association they never would have considered, well, they get on with life. They act like adults.