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.
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.
David Graeber argues that the inefficiency of barter in archaic society has been used by economists since Adam Smith to explain the emergence of money, the economy, and hence the discipline of economics itself. "Economists of the contemporary orthodoxy... propose an evolutionary development of economies which places barter, as a 'natural' human characteristic, at the most primitive stage, to be superseded by monetary exchange as soon as people become aware of the latter's greater efficiency." However, extensive investigation by anthropologists like Graeber has since then established that "No example of a barter economy, pure and simple, has ever been described, let alone the emergence from it of money; all available ethnography suggests that there never has been such a thing. But there are economies today which are nevertheless dominated by barter."
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.
Inevitably some people may feel like they were taken advantage of. One way to diminish inequities is to engage in dollar-for-dollar trades. For example, if you would like to trade your housecleaning service for someone’s couch, try to break down the goods and services to the dollar amount. If the two of you decide that the value of the couch is worth $200, why don’t you supply a gift certificate for $200 worth of housecleaning services? It’s a wise course and ensures all parties know what they are getting and what they are offering.
The same thing holds true of all other possessions; for barter, in general, had its original beginning in nature, some men having a surplus, others too little of what was necessary for them: hence it is evident, that the selling provisions for money is not according to the natural use of things; for they were obliged to use barter for those things which they wanted; but it is plain that barter could have no place in the first, that is to say, in family society; but must have begun when the number of those who composed the community was enlarged: for the first of these had all things in common; but when they came to be separated they were obliged to exchange with each other many different things which both parties wanted.
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).