We're crossing into new cultural space. Would implies that its the way things have become, but it still deserves some thought about the ultimate social ethics involved. Should implies that yes, of course he should be paid at this scale, it would be unfair otherwise. I think its a distinction and conversation worth having.
No, you misquoted mynegation. He said "which looks more like I though[t] it should be." As in, "which is similar to (what I expected/what it ought) to be."
There's still ambiguity, like you said, but its different ambiguity
English is not my native language and I actually meant "would be". However, I am not prepared to discuss whether this amount is justified or not. To me it looks pretty close to what board of directors _should_ pay Cook in order to keep him.