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I had this happen at a sketchy depanneur in Montreal last year. Swiped a debit card late at night, and next day had a empty $1000 deposit and real $500 withdrawal - oldest trick in the book. Bank returned the funds, no questions asked.

However, I don't think the apparent trustworthiness of the establishment has a lot to do with your likelihood of being compromised. In my local area, there's been several cases of the Interac/credit machines being replaced overnight in their entirety with fraudulent machines by sophisticated criminals. They've embedded transmitters etc in the machines that communicate the required information elsewhere. All this happens (in most cases) without the knowledge of the establishment or proprietor. Gas stations, fast food, convenience stores, etc.
 
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