Make the deal. After you've found a barter partner, get the agreement in writing. Make sure you detail what services or goods will be involved, the date of the exchange (or work to be done) and any recourse if either party reneges on their part of the deal. If you are working through a membership-based bartering association, they will likely provide all the structure and paperwork you need for the deal. 

Variable Merchant Gold - Adds more gold to select merchants. Merchants in major cities will no longer have the same amount of gold as their small-town counterparts. There are three levels with increasingly greater difference between the gold amounts for city & small town merchants. Personally, I would recommend leaving the Base Merchant Gold at vanilla values and choosing one of the Variable settings instead. You can stack the Variable settings by selecting multiple options in order to get even greater increases in merchant gold, but I really don't recommend doing this as I haven't balanced the values with this intention.
While some people may balk at an online community for finding babysitters, I know several parents who say it’s actually very difficult to find a sitter they can trust. BabysitterExchange started in 2000 as a babysitting co-op, and it has since expanded to the point that members use it to reserve time when they just have some errands run, need help tutoring their kids, or want a temporary house-sitter. 

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.[14]
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]
LITE VERSION - This version does not require SKSE or SkyUI. It does not include the changes to the barter settings, merchant respawn times, or the VendorGold lists. When installed, this version will activate automatically and uses the mod defaults for its settings. Please refer to the included README for full description of what is and is not included in this version.
Barter is a system of trade in which one party exchanges products, goods and services in order to obtain required products, goods and services possessed by another. In a barter system, no money exchanges hands between the buyer and the seller. Instead, both parties to the sale determine how much of a product a fair trade for another product or service. Since people assign different worth to different products, a barter system makes it difficult to decide how much of an item needs to be offered for another for the transaction to become a fair trade. Barter system was largely used long ago before the world developed the concept of currency for the exchange of goods. Nevertheless, the barter system is still prevalent today among nations, corporations, companies, individuals and businesses. The barter system makes trade easier for countries that experience large volatility in currency conversion and for countries that do not have sufficient financial resources, but have large volumes of commodities that can be traded for other commodities.
Bartering for goods and services is a centuries-old art. Recently, the idea of trading with your neighbors and within your community has received a big boost and taken on a modern spin. Combining our often-materialistic, ownership-based society with the Internet’s ability to bring buyers, sellers, and traders together, online bartering has sparked a wealth of new sites and communities.

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.

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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