In the United States, Karl Hess used bartering to make it harder for the IRS to seize his wages and as a form of tax resistance. Hess explained how he turned to barter in an op-ed for The New York Times in 1975. However the IRS now requires barter exchanges to be reported as per the Tax Equity and Fiscal Responsibility Act of 1982. Barter exchanges are considered taxable revenue by the IRS and must be reported on a 1099-B form. According to the IRS, "The fair market value of goods and services exchanged must be included in the income of both parties."
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.
No academics I talked to were aware of any evidence that barter was actually the precursor to money, despite the story’s prevalence in economics textbooks and the public’s consciousness. Some argue that no one ever believed barter was real to begin with—the idea was a crude model used to simplify the context of modern economic systems, not a real theory about past ones.
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.
In a small economy where individuals specialize in trades, they may find the process of setting up a centralized currency and maintaining it an unnecessary burden in order to trade. One option may be to use a commodity to exchange value between parties that want to trade goods or services and this is why gold and silver have been useful forms of currency in many cultures and times. Another option may be to use a barter system to trade.