Merchants are in a much better position to price this in than consumers. Merchants structurally execute a lot more transactions within a market vertical than consumers ever do.
If the merchant can't do that, because deals are simply too high value or aren't frequent enough, then insurance companies or intermediaries (e.g. payment processors) can pool risk across merchants, using actuarial techniques to assign a price to the insurance. For example, professional indemnity insurance for property transactions.