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From the point of view of a foreigner who attempts to speak correct English, this is a beautiful nightmare. Even the natives cannot agree among themselves.

Neverthefewer (/s), I try to use fewer when the items are obviously countable. But less seems to have a natural advantage of having one syllable only; people usually try to express their point as quickly as possible, and -1 syllable is better.

> I see fewer occurrences of fewer than less

Fixed that for you

Hannaford supermarkets in New England has "10 items or fewer". At first it seems strange since "10 items or less" is so common.

I often see "up to 10 items" which sidesteps the issue neatly.

Last time I was in a supermarket (Tesco near blackpool) I saw a sign for "5 items or fewer". I don't remember seeing an "or less" sign for a long time.