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 Economy had a long history of evolution. It was introduced in the pre-historic times for the systemization of the production and distribution of commodities and services among the existing population. In recent times, this age-old economic concept is widely prevalent among pre-market and pre-capitalist economies. A deep sense of reciprocation, together with substitution of the redistribution for market exchange characterizes Barter Economy currently.
He would have heard of channels and sandbanks, of natural features of the land useful for sea-marks, of villages and tribes and modes of barter and precautions to take: with the instructive tales about native chiefs dyed more or less blue, whose character for greediness, ferocity, or amiability must have been expounded to him with that capacity for vivid language which seems joined naturally to the shadiness of moral character and recklessness of disposition.
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.
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 historian Karl Polanyi has argued that where barter is widespread, and cash supplies limited, barter is aided by the use of credit, brokerage, and money as a unit of account (i.e. used to price items). All of these strategies are found in ancient economies including Ptolemaic Egypt. They are also the basis for more recent barter exchange systems.[17] 

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.