Trade in Skyrim is oversimplified and uninteresting. A particular type of merchant always has the same amount of gold and offers you the exact same prices as the same type of merchant in another part of the country. Merchants in small towns differ very little from those in the larger cities, and the only factors that affect price are your speech skill and any barter enchantments you might have. 

^ Homenatge A Catalunya II (Motion Picture). Spain, Catalonia: IN3, Universita Oberta de Catalunya, Creative Commons Licence. 2010. Retrieved 2011-01-15. A documentary, a research, a story of stories about the construction of a sustainable, solidarity economics and decentralized weaving nets that overcome the individualization and the hierarchical division of the work, 2011.


Bartering does have its limitations. Many bigger (i.e., chain) businesses will not entertain the idea and even smaller organizations may limit the amount of goods or services for which they will barter (i.e., they may not agree to a 100% barter arrangement and instead require that you make at least partial payment). But in an economic crunch, bartering can be a great way to get the goods and services you need without having to pull money out of your pocket.
Bartering does have its limitations. Many bigger (i.e., chain) businesses will not entertain the idea and even smaller organizations may limit the amount of goods or services for which they will barter (i.e., they may not agree to a 100% barter arrangement and instead require that you make at least partial payment). But in an economic crunch, bartering can be a great way to get the goods and services you need without having to pull money out of your pocket.
SOME SUGGESTIONS - With all these different variables, you may be wondering what the best settings are to achieve a good balance in your game. Of course this will depend on what you want. Many people (myself included) like to make trade more difficult. I also like to set the barter settings relatively close to de-emphasize Speech skill and place more importance on the Speech perks.
But the harm may go deeper than a mistaken view of human psychology. According to Graeber, once one assigns specific values to objects, as one does in a money-based economy, it becomes all too easy to assign value to people, perhaps not creating but at least enabling institutions such as slavery (in which people can be bought) and imperialism (which is made possible by a system that can feed and pay soldiers fighting far from their homes).

The Buy-day (Wheat) Ecological Life Associate summarizes a vision of life in Gezi as follows: "In our world, which is being poisoned and destroyed by consumer culture, we need sustainable and self-operating models of lifestyles, including a barter economy, ecological food production, arts and craftsmanship based on needs, renewable and effective energy use, agricultural models backed by society, permaculture, slow cities, transitional towns, eco-villages, district gardens and secondhand and recycling systems.
Still, Adam Smith really did seem to believe barter was real. He writes, “When the division of labour first began to take place, this power of exchanging must frequently have been very much clogged and embarrassed in its operations,” and then goes on to describe the inefficiencies of barter. And Beggs says that many textbooks sloppily seem to endorse this viewpoint. “They sort of use that fairy tale,” he explains.
^ Homenatge A Catalunya II (Motion Picture). Spain, Catalonia: IN3, Universita Oberta de Catalunya, Creative Commons Licence. 2010. Retrieved 2011-01-15. A documentary, a research, a story of stories about the construction of a sustainable, solidarity economics and decentralized weaving nets that overcome the individualization and the hierarchical division of the work, 2011.
Barter Network Ltd. is a proud member of The International Reciprocal Trade Association, IRTA, which is a non-profit organization committed to promoting just and equitable standards of practice and operation within the Modern Trade and Barter and other Alternative Capital Systems Industry, by raising the awareness and value of these processes to the entire Global Community. IRTA provide all Industry Members with an ethnically based global organization, dedicated to the advancement of Modern Trade and Barter and other Alternative Capital Systems, through the use of education, self-regulation, high standards and government relations. The Board of IRTA consists of Key Players in the Barter Industry, With Patti Falus President of Barter Network Ltd. being the only Canadian who sits on the Board.
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Economists since the times of Adam Smith (1723-1790), looking at non-specific pre-modern societies as examples, have used the inefficiency of barter to explain the emergence of money, of "the" economy, and hence of the discipline of economics itself.[3] However, ethnographic studies have shown that no present or past society has used barter without any other medium of exchange or measurement, nor have anthropologists found evidence that money emerged from barter, instead finding that gift-giving (credit extended on a personal basis with an inter-personal balance maintained over the long term) was the most usual means of exchange of goods and services.[4]


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