I see problems with both of your points of view.
Question: Isn't accurate also subjective? Since we don't have access to the master, how do we know when we have accuracy? Can't two speakers that measure similarly still sound quite different?
On the Cassandra Wilson argument, this is a hypothetical with all kinds of problems. How would Cass and her trio be recorded? If you want to make sure it will sound upstairs exactly like in your basement, it seems to me you will have a ton of work on your hands. Yet, in another sense, of course your recording of Cass and her trio will sound similar to the real thing -- it's a recording. So, I would argue that even if the recording sounds quite different from what you heard downstairs, it is likely that it will sound similar to you.