I don't think that the problem with the second sentence is as entangled as you state. Assuming that we know what the speaker is asking for when he asks for "prints" -- I assume she is asking for "prints" of art works -- then the real problem is determining what she will "like." But let me make the point that Jerry Fodor makes over and over again. Knowing what "she" will like is not the same as explaining why she likes what she likes or denoting all the cases that can instruct another person about my likes and dislikes. Knowing what "prints" she will like is not the same as knowing how and why we know what 10 prints she will like. The former may simply be a function of my familiarity with the person, the latter may take a lot of speculation about my empathy, her aesthetic judgment, etc. Similarly, the person asking for the "10 prints" may know what she likes but have no particular set of standards or rules to derive this judgment. This is only saying that to a certain extent the origins of our aesthetic likes and dislikes are not known by us and may never be known. Jerry Fodor made the more general point with more felicity than I do:
"There are lots of cases where we know more about how the world works than we do about how we know how it works. That's no paradox. Understanding the structure of galaxies is one thing, understanding how we understand the structure of galaxies is quite another. There isn't the slightest reason why the first should wait on the second and, in point of historical fact, it didn't."
If I make a statement to a good friend "Bring me 10 books I will like" we immediately have two problems. Do I mean books I have never read or books I have already read. In either case we are asking my friend to make a guess about my preferences and aesthetic likes and dislikes. My friend in bringing me the books may get it right, wrong or partially right and partially wrong. At that point - ten books by hand - I will try to express why I like this book and don't like that book. I may be inarticulate or over detailed in such expressions, but this is not at all the kind of obscurity that I am calling obscurantism.
Now let us take a different case. I say to a stranger, without further instructions, "Bring me ten books I will like." What is the stranger to do but try to interview me about the _kinds_ of book I like? If I am inarticulate or unselfconscious about these matters, then this is not a matter of obscurantism but a matter of inarticulateness and lack of thought. Often obscurity simply covers for a lack of thought, deception, self-deception or even (esp. in my case) laziness.
Now let us take an even more difficult case. Let us suppose I am creating a machine with a set of instructions that will always obtain for me the books I "will like" and/or "have liked" and/or "might like." This is the example that is closest to your case and I must say that it is a "technical" question and not a question of clear speech or unclear speech. It may be quite near impossible to provide such instructions so that they they such instructions are near comprehensive and result in a high success rate. It is not that my aesthetic judgments cannot be expressed clearly but rather that the contingencies and complexities of the "world" cannot all be reduced to denotative instructions that will cover all aspects of reality.
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