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.
Barter is a system of trade in which one party exchanges products, goods and services in order to obtain required products, goods and services possessed by another. In a barter system, no money exchanges hands between the buyer and the seller. Instead, both parties to the sale determine how much of a product a fair trade for another product or service. Since people assign different worth to different products, a barter system makes it difficult to decide how much of an item needs to be offered for another for the transaction to become a fair trade. Barter system was largely used long ago before the world developed the concept of currency for the exchange of goods. Nevertheless, the barter system is still prevalent today among nations, corporations, companies, individuals and businesses. The barter system makes trade easier for countries that experience large volatility in currency conversion and for countries that do not have sufficient financial resources, but have large volumes of commodities that can be traded for other commodities.
STOLEN GOODS - Don't expect any favors from Fences. Selling stolen items is going to cost you, so don't expect to get top dollar for ill-gotten goods. Tonila is exempt (actually all Thieves Guild & Dark Brotherhood fences are exempt, but in the vanilla game this just applies to Tonila). Any mod-added merchants who have been made members of the Thieves Guild or Dark Brotherhood faction will also be exempt. Options: -25% to -5% worse prices.
Anthropologists have argued, in contrast, "that when something resembling barter does occur in stateless societies it is almost always between strangers."[6] Barter occurred between strangers, not fellow villagers, and hence cannot be used to naturalistically explain the origin of money without the state. Since most people engaged in trade knew each other, exchange was fostered through the extension of credit.[7][8] Marcel Mauss, author of 'The Gift', argued that the first economic contracts were to not act in one's economic self-interest, and that before money, exchange was fostered through the processes of reciprocity and redistribution, not barter.[9] Everyday exchange relations in such societies are characterized by generalized reciprocity, or a non-calculative familial "communism" where each takes according to their needs, and gives as they have.[10]
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Anthropologists have argued, in contrast, "that when something resembling barter does occur in stateless societies it is almost always between strangers."[6] Barter occurred between strangers, not fellow villagers, and hence cannot be used to naturalistically explain the origin of money without the state. Since most people engaged in trade knew each other, exchange was fostered through the extension of credit.[7][8] Marcel Mauss, author of 'The Gift', argued that the first economic contracts were to not act in one's economic self-interest, and that before money, exchange was fostered through the processes of reciprocity and redistribution, not barter.[9] Everyday exchange relations in such societies are characterized by generalized reciprocity, or a non-calculative familial "communism" where each takes according to their needs, and gives as they have.[10] 

LOCATION - Prices are lower in smaller towns, but merchants also can't afford to pay you top septim for your goods. Cities are expensive, but there is more money to be made there. Merchants in cities charge higher prices when selling their wares, but they are also willing to pay more for premium goods in order to make sure that their shops stay well-stocked. The five major cities can now have their buying and selling rates set individually to reflect their size, wealth, access to supply and shipping routes, or status as a trading center.  

“Economic theory has always got to be historically bounded,” Beggs says. “I think it’s a mistake to think you’ll find the workings of modern money by going back to the origins of money.” He does point out that, while barter may not have been widespread, it’s possible that it happened somewhere and led to money, just given how much is unknown about such a large period of time.
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