While it may be free, there is no one monitoring the barter ads, so you must be aware of potential Craigslist scams, and realize that you are always at risk when it comes to meetups and exchanges. For example, about a year ago, I arranged to trade massage gift certificates for housecleaning. Since the individual was coming to my home, I was more nervous than usual. However, she offered good previous references, and we  arranged for a time to meet when my husband would be home, in case an odd, unexpected, or even dangerous situation arose.
Nowinska says one of the biggest challenges Swapsity faces is that new barterers think they have nothing to offer. So they offer bad trades. Yet most people have hundreds of skills—from cooking to networking to scrapbooking. The trick is learning to recognize the value of your skills, your knowledge and your talent. Bartering attaches value to things that are not always recognized, or highly valued, in a cash economy—often hobbies that people can’t make a living on but love to do. One Barter Babe trades her homemade canned goods for gifts—mostly other crafted items—she can give away at Christmas. A Swapsity member has traded pounds of fiddleheads she picks at her mom’s house in the country for feng shui sessions.
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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.

For instance, each time Apple releases a new version of the iPhone, the second-hand market for older versions of the iPhone enjoys a flurry of activity. However, you do have to be as careful with the barter of used goods as you would be with the purchase of used goods. Be sure everything is in working order and shows no signs of significant damage.

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).[15] 

The history of bartering dates all the way back to 6000 BC. Introduced by Mesopotamia tribes, bartering was adopted by Phoenicians. Phoenicians bartered goods to those located in various other cities across oceans. Babylonian's also developed an improved bartering system. Goods were exchanged for food, tea, weapons, and spices. At times, human skulls were used as well. Salt was another popular item exchanged. Salt was so valuable that Roman soldiers' salaries were paid with it. In the Middle Ages, Europeans traveled around the globe to barter crafts and furs in exchange for silks and perfumes. Colonial Americans exchanged musket balls, deer skins, and wheat. When money was invented, bartering did not end, it become more organized.
No, said Mises, for if taken back far enough, there comes a point at which money first emerges as a medium of exchange out of a pure barter economy Prior to this, it is valued only for its non-monetary uses as a commodity The demand for money is therefore pushed back to the last day of barter, where goods are traded only in direct exchange, and where the temporal element of the regression theorem ends It is in this way that all charges of circularity are obviated.

Yet after three years with the firm, she was dissatisfied. She was spending all her time advising millionaires when she wanted to work with average Torontonians, especially women. She couldn’t help noticing that most of her female friends were broke, confused and floundering. Online, her social media feeds were filled with panicky talk of recession budgets and empty wallets. There was one problem: those women couldn’t afford to pay her, and she certainly couldn’t afford to work for free. “I really wanted to do it,” she says, “but I couldn’t figure out a business model.”
The Internal Revenue Service (IRS) considers bartering a form of revenue and something that must be reported as taxable income. Under U.S. generally accepted accounting principles, or GAAP, businesses are expected to estimate the fair market value of their bartered goods or services. This is done by referring to past cash transactions of similar goods or services and using that historical revenue as a reportable value. When it is not possible to accurately calculate the value, most bartered goods are reported based on their carrying value.
Simmons learned how to ask after one Barter Babe, a veteran barterer, told her she needed to post a wish list. Following the advice, she eventually got not just one bike but two (one for her and one for Matt), a TTC pass, yoga lessons, a haircut and food she wanted to eat, among hundreds of other things. Simmons made exceptions for some unique trades, too, such as both circus performance training and butter churning lessons, the latter of which she now barters as a skill to others. She even worked up the nerve to approach local businesses in person, armed with a business case for barter. One café near her apartment traded a month’s worth of morning coffee for a financial session; a boutique hotel, Hotel Ocho at Queen and Spadina, took a financial seminar luncheon for its employees in return for an overnight stay for Simmons’s parents, who were celebrating their 35th anniversary.
Other anthropologists have questioned whether barter is typically between "total" strangers, a form of barter known as "silent trade". Silent trade, also called silent barter, dumb barter ("dumb" here used in its old meaning of "mute"), or depot trade, is a method by which traders who cannot speak each other's language can trade without talking. However, Benjamin Orlove has shown that while barter occurs through "silent trade" (between strangers), it also occurs in commercial markets as well. "Because barter is a difficult way of conducting trade, it will occur only where there are strong institutional constraints on the use of money or where the barter symbolically denotes a special social relationship and is used in well-defined conditions. To sum up, multipurpose money in markets is like lubrication for machines - necessary for the most efficient function, but not necessary for the existence of the market itself."[13]
Other countries though do not have the reporting requirement that the U.S. does concerning proceeds from barter transactions, but taxation is handled the same way as a cash transaction. If one barters for a profit, one pays the appropriate tax; if one generates a loss in the transaction, they have a loss. Bartering for business is also taxed accordingly as business income or business expense. Many barter exchanges require that one register as a business.