I think the idea of voluntary states/taxation will be necessary to bridge the gap between a world of nation states and free anarchy. From the early days of rape and pillage to the charming dispositions of swindlers, taxation has evolved to the point most people doubt it is compulsory.

Now, I don't particularly like the idea of a tax on all land being called voluntary. Unless you're a fish or a seasteading billionaire, it'd be identical to the present day minus all the other compulsory taxes. Besides,

The underlying premise, that the state rightfully owns the earth, would just be a reset button on state power. This belief in states is entirely cultural. It is William Blake's "mind-forged manacles" and if people don't stop believing this bullshit no amount of political reform is going to be enough. The problem with a free market society coexisting with a government is the government will grow incredibly powerful by feeding off its productive people. The U.S. is perhaps the most historically relevant example of this. Additionally, land and future taxation can be used as collateral for credit. It's a recipe for unconstrained growth.

I think another means of facilitating this transition is too simply relax government control and allow businesses to step into traditional government roles. E.g FedEx or UPS. If the service is necessary and needed, people will pay for it willingly. As I see it, nothing major needs to be undone or tore down. Time and consumer choice would make the government service obsolete. Let them fade away.

Another factor we mustn't overlook when we ponder a free society is the very interface we are conversing through. The internet completely changes what future self-government will look like. We can see glimmers of it nowadays, but who knows what a couple of centuries of this will do to our political systems.