This example doesn't seem the best way to judge the matter because mixing up appointments is never a desirable thing, and so we assume some nuance of complaint or dissatisfaction whatever the phrasing A better example might be "He's always telling me about his family problems" / "He always tells me about his family problems". In this case we can see, all other things being equal, that the former does have more of a nuance of complaint than the latter. g.
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