I have to say that I am not entirely sure what the message is. There are so many things mixed in. The whole topic is interesting, though, and pretty complex I guess. I am sure that the context will be more clear when the questions start to come in :-)
When I am at it, I think that the context where we are asking the question really matters, doesn't it? In formal logic a statement can be true, false, independent, contradiction and what not and it only depends on the underlying theory. But logic is a funny thing. As one of our university professors used to say during the introduction to logic: "All pink elephants in this room have wings and they can dive like a submarine." And he was right! :-)
Leaving the formal part behind and going a bit closer to humans, I remember a story of Carl Gustav Jung travelling around Africa. He was researching what people there think about what they actually use for thinking. He asked a local chief and the chief was surprised to be asked such an obvious question. He pointed to his heart.
This seems pretty interesting to me. Talking about questions, is there actually any common context for all humans to base their answers on? Is it even worth it to be asking deep questions and expecting someone else to give us the answer? How to approach the questions that cannot be answered in words? There are all these Zen stories that came to existence for this purpose. You hear a story, something clicks and you are enlightened. A great mystery, that a story can tell so much and hit your soul directly.
Anyway :-) I agree that the process of questioning and trying to find the answer is probably the most interesting part. And it is more fun the deeper you go. You may think that you have arrived to the final and stable conclusion. Now you know what the true purpose of life is. But then someone comes, or an experience comes, and it completely shatters your story and your mental map collapses like a house of cards. Damn, I got trapped in ideas again, unable to see the truth, but I will try better next time! And a month later, you are again watching your personal story fall to pieces. Hahahah. Very funny and the most horrific thing at the same time.
I am wondering what is there at the end. Is there DA TRUTH? Do you find the answer? Or do you stop asking questions? Where are we actually trying to get? Describe the process? Then what? Ask more questions? Why not to ask the most difficult questions first? Then what? Why am I being pushed into this never-ending process of thinking and researching and why some people don't give a shit? What is there to find? Something? Nothing? What does it mean to be lost? Is there anything like being lost? Am I being lost? Is everyone except me lost? Did everyone find the truth? How come my truth is not your truth? What is truth then? Mine? Yours? Both? Neither?
This is the moment to shut up, sit down, take a deep breath and start meditating I guess :D
I described here some of the assumptions I made in the original post. From them it follows that the only universal context for the whole humanity is the reality itself, because any other context is subjective. I also touched the "my truth != your truth" problem. Hope my explanation won't create even more confusion :-)
About asking the most difficult question first, I think you would get stuck pretty early. It seems to me that a good approach might be to always have a whole spectrum of unanswered questions, with increasing difficulty. Some of which could be addressed today, some within a week, within a month, year, lifetime (the exponential increase is intentional), as long as there are some left unanswered.
Nobody knows what the reality is actually, you can ask any quantum physician :-) I have been reading, though, about what this common ground could be and it seems that it could be consciousness itself. Some people are talking about changing the current paradigm to put consciousness above matter. Doesn't even seem to be anything new really. Peter Russell gate a rather interesting talk about this.
Talking about the sorting of questions, for me it seems that there are multiple completely different types of questions so to say. For example talking about consciousness, how do you want to touch that field without simply using your consciousness and nothing else? These questions are completely different from those answerable using mere words to me. And researching consciousness is a funny thing. You never know what and when is going to happen. Try to come up with a sorting :-)
Neither :)