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The answer is yes. Before the 1990s, there were was a lot of casual business. My San Francisco residence was rented to my flatmate entirely on a verbal contract (which created problems in the aughts, when utility companies were modernizing their service). This kind of casual business works well when everyone is friendly or acting in good faith, but it leaves fewer protections from fraud.
In rural parts of the US, there were regions in which there was little enough cash flow that barter was routine. And then farms often would have enough extra produce they would look for neighbors to give food to, rather than dumping it.
I'd say we'd have organized crime to thank for the necessity of making transactions a lot more secure and a lot less anonymous, but that's really only the justification. It's law enforcement that has turned to the same rackets that were the purview of mobsters. Not only are grocers no longer able to give away one-day expired food to homeless and impoverished folk, but kids risk legal trouble just by running a lemonade stand on a hot day.
Thank you for sharing your experience and insights!