Just as with most things, there are disadvantages and advantages of bartering. A complication of bartering is determining how trustworthy the person you are trading with is. The other person does not have any proof or certification that they are legitimate, and there is no consumer protection or warranties involved. This means that services and goods you are exchanging may be exchanged for poor or defective items. You would not want to exchange a toy that is almost brand new and in perfect working condition for a toy that is worn and does not work at all would you? It may be a good idea to limit exchanges to family and friends in the beginning because good bartering requires skill and experience. At times, it is easy to think the item you desire is worth more than it actually is and underestimate the value of your own item.
Barter-based economies are one of the earliest, predating monetary systems and even recorded history. People can successfully use barter in many almost any field. Informally, people often participate in barter and other reciprocal systems without really ever thinking about it as such -- for example, providing web design or tech support for a farmer or baker and receiving vegetables or baked goods in return. Strictly Internet-based exchanges are common as well, for example exchanging content creation for research.
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.[2] "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development of economies which places barter, as a 'natural' human characteristic, at the most primitive stage, to be superseded by monetary exchange as soon as people become aware of the latter's greater efficiency."[3] However, extensive investigation by anthropologists like Graeber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."[4]

While one-to-one bartering is practiced between individuals and businesses on an informal basis, organized barter exchanges have developed to conduct third party bartering which helps overcome some of the limitations of barter. A barter exchange operates as a broker and bank in which each participating member has an account that is debited when purchases are made, and credited when sales are made.

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.
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In his analysis of barter between coastal and inland villages in the Trobriand Islands, Keith Hart highlighted the difference between highly ceremonial gift exchange between community leaders, and the barter that occurs between individual households. The haggling that takes place between strangers is possible because of the larger temporary political order established by the gift exchanges of leaders. From this he concludes that barter is "an atomized interaction predicated upon the presence of society" (i.e. that social order established by gift exchange), and not typical between complete strangers.[13]