Personally, I would be comfortable with 0 confirmation transactions up to a thousand dollars.
Why would you? Some businesses live of high-volume low-value transactions (grocery stores, bookstores, etc.) I'm sure they care if you pay or not.
Unfortunately
"I wouldn't care personally" is not a solution and this is a tough barrier for in-person merchants to adopt Bitcoin.
I wouldn't even trust a guy showing me his mobile-wallet. It could be just a facade that does nothing behind the curtains.