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.
Throughout the 18th century, retailers began to abandon the prevailing system of bartering. Retailers operating out of the Palais complex in Paris, France were among the first in Europe to abandon the bartering, and adopt fixed-prices thereby sparing their clientele the hassle of bartering. The Palais retailers stocked luxury goods that appealed to the wealthy elite and upper middle classes. Stores were fitted with long glass exterior windows which allowed the emerging middle-classes to window shop and indulge in fantasies, even when they may not have been able to afford the high retail prices. Thus, the Palais-Royal became one of the first examples of a new style of shopping arcade, which adopted the trappings of a sophisticated, modern shopping complex and also changed pricing structures, for both the aristocracy and the middle classes.
There are several disadvantages of the barter economy. Firstly, there has to be double coincidence of wants for exchange to take place. Again the problem of indivisibility of commodities comes in the matter of exchange. Basically such disadvantages and many more called for the emergence of money. Money is used as a common medium of exchange and store of value.
Bartering allows individuals to trade items that they already have but are not using for items that they need while keeping their cash on hand for expenses that cannot be paid through bartering such as a mortgage, medical bills and utilities. Bartering can also have a psychological benefit because it can create a deeper personal relationship between trading partners than a typical monetized transaction. Bartering can also help people build professional networks and market their businesses.
Search for bartering partners. After you know what you have to offer and exactly what you need/want in a barter situation, find a bartering partner. If you don't have a specific person or business in mind, try word of mouth. Let your friends, colleagues and social network know about your specific need and what you want in a barter situation. Use Facebook, LinkedIn and Twitter.
Since the 1830s, direct barter in western market economies has been aided by exchanges which frequently utilize alternative currencies based on the labor theory of value, and designed to prevent profit taking by intermediators. Examples include the Owenite socialists, the Cincinnati Time store, and more recently Ithaca HOURS (Time banking) and the LETS system.
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Barter is a system of exchange by which goods or services are directly exchanged for other goods or services without using a medium of exchange, such as money. It is distinguishable from gift economies in that the reciprocal exchange is immediate and not delayed in time. It is usually bilateral, but may be multilateral (i.e., mediated through barter organizations) and usually exists parallel to monetary systems in most developed countries, though to a very limited extent. Barter usually replaces money as the method of exchange in times of monetary crisis, such as when the currency may be either unstable (e.g., hyperinflation or deflationary spiral) or simply unavailable for conducting commerce.
As Orlove noted, barter may occur in commercial economies, usually during periods of monetary crisis. During such a crisis, currency may be in short supply, or highly devalued through hyperinflation. In such cases, money ceases to be the universal medium of exchange or standard of value. Money may be in such short supply that it becomes an item of barter itself rather than the means of exchange. Barter may also occur when people cannot afford to keep money (as when hyperinflation quickly devalues it).