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.
Not sure who your friends are? Listen for comments like "You've been a good friend to me" or "It's a fine day with you around." You can also check using the console, just select the NPC in question and enter: player.getrelationshiprank Be aware that not all favor quests result in an increase in your relationship with the person. You can use this mod to help fix some of those relationship oversights.
The Owenite socialists in Britain and the United States in the 1830s were the first to attempt to organize barter exchanges. Owenism developed a "theory of equitable exchange" as a critique of the exploitative wage relationship between capitalist and labourer, by which all profit accrued to the capitalist. To counteract the uneven playing field between employers and employed, they proposed "schemes of labour notes based on labour time, thus institutionalizing Owen's demand that human labour, not money, be made the standard of value."[16] This alternate currency eliminated price variability between markets, as well as the role of merchants who bought low and sold high. The system arose in a period where paper currency was an innovation. Paper currency was an I.O.U. circulated by a bank (a promise to pay, not a payment in itself). Both merchants and an unstable paper currency created difficulties for direct producers. 

SOME SUGGESTIONS - With all these different variables, you may be wondering what the best settings are to achieve a good balance in your game. Of course this will depend on what you want. Many people (myself included) like to make trade more difficult. I also like to set the barter settings relatively close to de-emphasize Speech skill and place more importance on the Speech perks.
Michael Linton originated the term "local exchange trading system" (LETS) in 1983 and for a time ran the Comox Valley LETSystems in Courtenay, British Columbia.[22] LETS networks use interest-free local credit so direct swaps do not need to be made. For instance, a member may earn credit by doing childcare for one person and spend it later on carpentry with another person in the same network. In LETS, unlike other local currencies, no scrip is issued, but rather transactions are recorded in a central location open to all members. As credit is issued by the network members, for the benefit of the members themselves, LETS are considered mutual credit systems.
PaperBack Swap is exactly what it sounds like: a place to swap paperback books. Currently, more than half a billion books are available for trade on the site. Just list the books you don’t want anymore and other members will find them. When someone requests one of your books, you just mail it out and then choose any available book that you want to receive. Swapping is easy, and membership is free.
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.