"better according to some shared, motivating standard or procedure of evaluation",

I broadly agree. My thinking ties shoulds and musts to rules and payoffs. Wherever you are operating a set of rules (which might be as localised as playing chess), you have certain localised "musts".

It seems to me that different people (including different humans) can have different motivating standards and procedures of evaluation, and apparent disagreements about "should' sentences can arise from having different standards/procedures, or disagreement about whether something is better according to a shared standard/procedure.

I'm very resitant to the idea, promoted by EY in the thread you refenced, that the meaning of should changes. Does he think chess players have a different concept of "rule" to poker players?