The first trick question in this passage deals with taxes. Roman taxes were debated quite a bit in Jewish society, mostly because the Jews saw the Romans as foreign occupiers and didn't want to give them anything. There are various teachings about taxes in the Talmud, and Jewish teachers were not of one mind. In the gospel stories, words put in Jesus' mouth are often very similar to the words of prominent Jewish teachers, primarily those who agreed with the views of Hillel the Elder, a well-known Jewish teacher who lived a generation before Jesus' supposed lifetime. From the perspective of these teachers, worrying about taxes was often seen as a distraction from living the kind of life one was supposed to live. The authors of Mark seem to echo this, although the answer given by the character of Jesus is far from clear.
This business about giving to Caesar what belongs to Caesar and giving to God what belongs to God is so subject to interpretation that it resolves nothing at all. It is the sort of answer that essentially says, "make up your own mind about the matter," but has all the appearance of a wise and clever answer. Many people seem to enjoy drawing the conclusion that everything belongs to God, but then they continue to live their lives as though they have rights of ownership. Some people imagine that they have been granted "stewardship" over a portion of what belongs to God, which entitles them to act as surrogate owners of a piece of God's property while he isn't using it. All of this, of course, is being taken completely out of the context of first century society, in which private ownership wasn't even a consideration. Kings and lords owned land and everything on it; the people were granted rights to live and work on the king's or lord's property. One cannot directly translate the lessons of a feudal society into an economic system that hinges on the concept of private ownership.
If we approach the concept with the idea that gods don't need money or property, not least of all because they are the products of human imagination, the answer to such questions becomes much easier to address. Pretending that there is a supernatural who must be taken into consideration with all human decisions is often just an excuse for people to claim entitlements that otherwise seem completely without foundation. Should one pay taxes? Does one benefit at all from the services those taxes fund? What would be the most equitable, just, and compassionate response to the needs of one's society? Is one prepared to suffer the legally enforceable penalties for non-payment of taxes? These questions may evoke differences of opinion, but they lead toward a more warranted response to taxation than questions based on subjectively interpreted religious constructs.
The second challenge is also an obvious trick question, pertaining to myths about the afterlife. One might think that the challenge was about Levirate marriage, but if the gospel writers were concerned about that issue, they would have had Jesus comment on that instead of on the conditions of the afterlife. Lots of people still make a considerable amount of money publishing books and speaking about an afterlife. It's very convenient, since no one can really contradict what anyone claims about afterlife, since any claims come out of the human imagination. Jesus' answer plays into the mythology of the day because the gospel authors bought into the mythology of the day.
In the twenty-first century, we wouldn't ask, "How can Pegasus fly, being the size of a normal horse?" If someone were to ask such a question, though, we would have a choice. We could say, "Pegasus has lighter bones than a regular horse, so he doesn't weigh as much as a normal horse." Or we could say, "There's no such thing as a flying horse. That's a story that came out of human imagination. Don't worry about how the horse flies, just enjoy the story for what it is." When it comes to questions about the afterlife, we seem much more inclined to make up answers that sounds good, even though we have no evidence or justification outside of our own imaginations. It's certainly a marketable option. If we were more honest, we might say, "There's no such thing as an afterlife. When we die, we're done. But if there were an afterlife, I would hope for it to be like _________." Instead, like the gospel writers, we pretend to know something that we don't know.
This doesn't seem like such a bad thing on the surface. Believing in an afterlife gives people comfort and hope, right? Well, sort of. If your heat goes out in the dead of winter and the temperature stays way below freezing for weeks on end, you might be comforted by the idea that the heat will come back on (or even that a supernatural will protect you from the cold). Being comforted and hopeful doesn't bring the heat back on, though. If you believe in a pleasant afterlife, maybe you will be comforted and hopeful enough that you won't mind freezing to death. That seems delusional, but there are an awful lot of people who spend an awful lot of money trying to communicate with people who have died, or who resist opportunities to improve their well-being because they believe that their afterlife will be filled with rewards for the hardships they face in this life. If comfort and hope are based on imaginary claims, then the comfort and hope are insubstantial and potentially harmful.
The gospel writers do indicate something important in this exchange, however. The idea that the Jewish god was not the god of the dead but of the living can have some traction beyond satisfying this trick question about mythology. Our deepest, most noble selves are not adversaries; deep down inside, we are not lifeless. While we are sometimes our own worst enemies because of the false beliefs we develop about ourselves, other people, and the world around us, at our core, we know what makes life satisfying. We hold the truths about our passions and we know what the best possible versions of ourselves would look like. When we turn inward, we are not looking to discover all the things we have done wrong or catalog regrets and failures. Connection with ourselves places us within a context of growth, of becoming, of abundant life. We don't need to be bolstered by mythology to create the lives we most want -- to develop into the best versions of ourselves possible.
When we consider the third challenge in this passage, the gospel writers have thrown an easy pitch. It was a major theme of Hillel the Elder (and the rabbis that followed his school of thought) that the whole of the Torah could be expressed in what we know as the "golden rule." So, this idea that the greatest commandments were to love Yahweh and to love others was a prominent ethic in first century Judaism. If this question had actually been asked of a historical Jesus, perhaps it was merely a way of asking, "Does what you teach agree with what I believe?" Perhaps all of these challenges were originally along those lines. The end result is that we get an impression that our loving actions are much more important than our religious practices.
Recontextualizing this portion of the passage to accommodate the understanding that there are no supernaturals for us to love or worship, and that any characteristics we call "divine" are human characteristics that all people possess, we wind up with something like this:
One man approached, overhearing the subject matter of their conversation, and seeing that the teacher was wise, he asked him, “What's the most important thing?” The teacher answered, “The most important thing is, ‘Pay attention: at your core, you are capable, beautiful, and creative; love yourself enough to connect with your deepest, most noble self and become the best possible version of yourself.’ The second most important thing is this, ‘Love other people with that same depth of connection, and see the capability, beauty, and inspiration in everyone else.’ There is nothing more important than these.”
The question about the mythical messiah being David's son is a bit anticlimactic, but it seems to belong to this passage, at least as the passage was edited and rewritten over generations before it became the document we read today. It's a nonsense question, based on a poetic expression in a psalm. The psalms are as much poetry as anything else, and their language is poetic language. When we read that Yeats had a fire in his head, or that a trout he caught turned into a girl, or that he was going to pluck the silver apples of the moon and the golden apples of the sun, we don't take all of that literally. We don't believe that Yeats' head actually contained a fire, or that he actually caught a trout that actually turned into a girl. We don't believe that the moon and the sun have silver and gold apples. Such questions would miss the point of the poetic language. The same is true of the psalms. Perhaps that was the point of the gospel authors: all of these challenges are as silly as trying to pick apart the poetic language of a psalm and draw some sort of logical conclusion.
If there is anything to be gleaned from this passage, it is that we can get distracted by theoretical debates that have no foundation in reality, and in so doing, we can miss the more important things: Being the best versions of ourselves possible and empowering the people with whom we share this planet to do the same. The most important thing we can contribute to the world is to know ourselves well enough to recognize what we are really passionate about, to nurture our own ability to bring our own selves forward, and to create the kind of world we most want to live in. Incidentally, this also involves dismantling the fears and the false beliefs about ourselves and other people that keep us from connecting with our deepest, most noble selves. The second most important thing we can contribute to the world is to be present in the lives of the people around us. To see them as human beings of inherent worth, to listen to their dreams and challenges, to bear witness to their creativity and beauty, and to encourage and empower them as they grow and develop into the best versions of themselves possible. This is a lifelong engagement, and it's also what brings meaning to our lives. It's easy to get distracted by clever questions and answers, but how well we love ourselves and how well we love others is the answer to the most important questions.