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.
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).
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.
An alternate currency, denominated in labour time, would prevent profit taking by middlemen; all goods exchanged would be priced only in terms of the amount of labour that went into them as expressed in the maxim 'Cost the limit of price'. It became the basis of exchanges in London, and in America, where the idea was implemented at the New Harmony communal settlement by Josiah Warren in 1826, and in his Cincinnati 'Time store' in 1827. Warren ideas were adopted by other Owenites and currency reformers, even though the labour exchanges were relatively short lived.
Commercial activities in a Barter Economy are restricted mainly between two nations or business communities. The benefit of this economy is felt mostly in times when the existing financial system of a country remains unsuccessful in assessing the economic worth of various commodities. As a matter of fact, Barter Economy best serves a nation during hours of financial emergencies.
Remember back in school when kids would swap juice boxes for chips, or cookies for Twinkies? Even children have an innate sense that the comparable value of cookies to Twinkies is in the eye of the beholder. To the kid who gets cookies every day, the elusive cream-filled cake treat is worth more than a few, and he realizes his friend might feel differently.
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.