Flavor keeps them coming back. Sometimes a free sample is necessary. Cherry tomatoes lend themselves well to sampling. I have given away slicer size tomatoes before, when customers were skeptical that they tasted good. They always come back and buy more; often the other customers will hear their compliments and buy because of that themselves.
Speaking of "onerous regulations," health codes over cut up samples of anything tend to be strict. But handing a person an uncut tomato does not trigger the rules for samples.
The best way I have found to compete with the other vendors is simply to avoid competing. Sell something different. It's the same with selling plants or the actual tomatoes. I let the other vendors have the customers who want $1.50 six-packs of Celebrity; I sell dwarfs and heirlooms. Later in the summer, the other vendors will show up with truckloads of what I call 'red baseballs.' I don't. If I even sell any big red tomatoes at all, they will be labeled as the rare heirlooms that they are.
By the way, if you don't spray at all, customers love a sign that says "pesticide-free."
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