"a <= b" and "b <= a" being simultaneously true is fine because of the '=' part; I presume you mean that "a < b" and "b < a" being simultaneously true is indicative of a problem (which it is).
On the other hand, "a <= b" and "b <= a" being simultaneously false is sometimes compulsory (IEC 60559 floating point requires that all comparisons involving NaNs, including comparing a NaN to itself, return false.)
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