Maybe make it a statement as well, instead of "Can you?".
When mine was 6, I said "Would you please feed the dog?" and he responded "Wait, are you asking me or telling me?". I said I was telling him in a very nice way.
And, I agree about broad in some cases "Check the upstairs for dirty dishes and bring down any you find". But, in some cases, I have to be very specific. Once I said to him, bring me all the towels from your bathroom so that I can wash them. He did just that - ALL the towels, clean and dirty. To me, it was clear that I would only want to wash dirty ones, but to him, that "all" meant everything.
If there are ideas to help mine learn to extrapolate or generalize, I would appreciate that as well. As in your example, from "check the upstairs for dirty dishes and bring them to me" he would see a dirty cup in the living room and automatically pick it up and bring it as well.
And, yes, very frustrating here as well.
