There are historical examples of classless societies: the primitive communism that existed before agriculture was invented, is a counter-example to the theory that the biological nature of humans makes class-based societies inevitable.
If you hold prehistoric, pre-agriculture human communal life to be a model, then you need to destroy civilization (and throw away your pandora) to achieve it. The neolithic revolution - the birth of agriculture - was achieved only due to the establishment of property rights - the right of a farmer to invest his time and labor on a claimed piece of land to produce an excess of nourishment.
"Three successive (though overlapping) proto-historical cultures arose in northern Mesopotamia: the Hassuna, Samarra, and Halaf cultures. All three made great strides in art, trade, and the technologies of agriculture, building, implements, pottery, and even irrigation.5 And not one of them showed any signs of having a central government". The subsequent specialization of work naturally led to some people acquiring more property than others. This is deeply distasteful to socialists and Marxists -- that someone is allowed to keep the result of their labor. (and I consider that a deeply
sick ideology.)
That is why I don't think it is possible to arrive at a true classless society overnight -- I think it will take several generations before such a "
withering away of the state", to quote Engels, is possible.
1) I think you are right that it will take generations. But the "withering away of the state" is precisely what libertarianism and classical liberalism aims for. Historically, limiting the powers of the state is precisely what made some societies prosperous. The instances in which the powers of the state were reduced occurred due to free-market, classical liberalism. The examples throughout
Europe and
Asia abound, where the right of the rulers to confiscate property was limited by classical liberal ethics and law. All socialist endeavors, even those led by self-proclaimed Marxists, have enhanced the power of the state and created a class of
priveleged bureaucracy.
2)
A classless society is only achieved by a free society, absent overlords and underlings. There is no such thing as a capitalist "class". In a free market, every enterpreneur is a capitalist, everyone who invests in stocks or bonds is a capitalist. (EDIT: EvilDragon is a capitalist). If a worker wants ownership of the means of production, he or she need only invest in his or her own company. (Why on earth would it be better to
force workers to invest in their own company, even if they feel there are better uses for their money?) In a free market society, the industrious and inventive poor can become well-off, even rich, and the rich can make grevious mistakes and become poor. People are not born "stuck" in a particular class.
3) The market allows for companies to experiment with different types of organization. Valve, Inc. is an example of a company with
no bosses, no managers at all.
4) An enterpreneur/capitalist in the free market is not an oppressor, because he competes
not only with others to provide goods and services at an acceptable price, but he competes with other enterpreneurs to attract workers with agreeable wages and working conditions. No system of conscription (forced labor, forced military service) provides comparable working conditions. (EDIT: Under
interventionism or
mercantilism some companies enjoy special priveleges and protections by the state, which functions as the oppressor. For example, see the US military interventions in Central America to benefit United Fruit: This is an anathema to libertarianism and classical liberalism)
On top of that, discussions on prehistoric ages do not make much sense since the fabric of society is proportional to the density of people living in the same place. The more you have people, the more a system is needed for everyone to live together peacefully.
This is a dangerous way to phrase what you mean. Socialists of all types clamor for "systemization" - planning by "experts", usually with the argument that some new aspect of "modern society" requires it. In reality what happens naturally as population density increases, is capital accumulation, specialization of work, and trade of produced goods and services. Calling this evolutionary process a "system" or saying a "system" is needed plays into the rhetorical hands of socialist planners. To live together peacefully you just need to outlaw violence, theft and fraud and have some means for providing security.