Glass Lamborghini Problem

This post is for libertarians, ancaps, or objectivists, but anyone is welcome to opine.

So imagine the ideal deregulated, privatized society. The haves aren't forced to subsidize the have-nots. In theory, if one person violates the property rights of another then they should be made to pay restitution (who does said enforcing is another question for another day).

Imagine a society evenly split between haves and have-nots. It's fashionable for the haves to own $500,000 supercars, both expensive and relatively fragile, to the point where a fender bender could cost $30,000 to repair. You are a have-not with a regular car. One day, while driving, you're distracted. You will spent countless hours of your life behind the wheel, so it was bound to happen at some point; you're not drunk or on your phone. Perhaps you're younger and have less experience driving. In any case, you were following this guy a little too close, and you didn't notice in time when he slowed down to turn. And so, you rear-end him. Fate flips a coin, and it turns out the car you hit was a supercar.

In today's world, there are rules protecting you from being taken through the cleaners for an honest accident. But how should it work in this libertarian world? If you're 100% on the hook for a $30K repair bill, then in practice doesn't that amount to someone else's property rights aggressing against yours? If not, then explain.

Is the problem solved by insurance? If so, then would it be expected that the driver of the supercar fully insure his own vehicle against damages? Is this the ethically right policy? What liability should the driver of the other car have? Would the right outcome ensue in a free market?

If you are guilty for the damage, you pay for the damage. Its not that hard.

Maybe car accidents need a debate about who is guilty given the retarded traffic laws currently existing, but the actual causation law usually says that if A could have avoided doing something, but didnt, A is guilty.

This sort of thing is why I stopped being a libertarian. Other thought experiments were people shooting a gun in the air to celebrate new years and the threat of falling bullets. In a libertarian society you create a lot more danger, and would only punish the guy whose bullet fell on a child, but it would be impossible to find the guy because you can't bam the shooting of a gun in the air so it would be wide spread.

I have a bout 3 thought experiments that turned me more towards conservatism.  One of the biggest reasons may have been that the ideology only works if you do not allow your populations minds to be polluted towards socialism and it is impossible to prevent that without violating your own principles.

This is where paleo conservatism comes in. It does allow some modifications to a generally libertarian philosophy that is responsive to threats to a generally libertarian society. 

Other outside threats include trade with other countries that are willing to operate under a loss for market capture and 

Other issues include the ideology when taken to uts logical conclusion is actually quite oppressive (though this is more difficult to outline)

And

In a libertarian society you could easily end up in the same exact society we have now so it's hard to critique this society. (I will get into why at some later point)

Yes, pure liberty is as bad as a pure dictatorship. Some dangerous things need regulation, but regulating lemonade stands is way too far.

Its true that many problems rise in anarchy. Like, its difficult to establish who gets to decide when two freedoms contradict. Still, anarchy is the closest thing there is to greatest freedom for all. I suggest society should gradually progress towards anarchy so all problems are resolved one by one. Like, every solution to a problem should be that such solution upholds freedom, doesnt reduce freedom.