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I think the reason, at least primarily, that it works differently for Plus is the following from its documentation: Unlike other functions, Plus applies built-in rules before user-defined ones. It may seem a little obscure, because perhaps we don't know all the rules, but these two are mentioned explicitly: Plus[] is taken to be 0. ...


START EDIT: "Sort by default orders integers, rational, and approximate real numbers by their numerical values." Since your expressions are none of these, you should expect the "canonical order" to likely be other than numeric. "In most cases, NumericQ[expr] gives True whenever N[expr] yields an explicit number"; consequently, NumericQ will return True for ...

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