Maybe I can offer some helpful commentary on this thought-provoking discussion between OzSpen and Zeena.
What's happening is that you two are drawing, respectively, from both the mainline wisdom tradition AND the counter-tradition that arose as a response to it. I suggest that BOTH are present in the Old Testament and NEITHER is complete without the other.
Wisdom literature includes the book of proverbs, a number of key psalms (e.g. Ps. 1), and other scattered references through the OT. Unlike, say, the Pentateuchal or Prophetic traditions, the story of Israel as a nation isn't the focus in Wisdom. Rather, it looks at God's relationships in smaller communities -- villages, social networks, families, individuals. In this context the question isn't "What is God doing with Israel?" but rather "What is God doing with us?" Instead of analyzing the dynasties of a nation, her foreign policy, her kings and her prophets, things like money, listening to elders, temptations, laziness, food, favor -- things that apply to almost everyone at a personal level -- are considered instead. What does daily, mundane life have to do with God? How is God connected to my routine, my life from birth to death, my place in my family, my place in my community? How does faith in God affect me on a practical level?
It is God's desire for universal happiness and blessedness that is relevant here. Certain habits and behaviors are said to be wise if they are regularly associated with this blessedness; likewise, foolish behaviors are marked by working against the grain and bringing death, pain, bitterness, sadness, frustration and anger. These evaluations of mundane lifestyle, now with a cosmic significance -- either working in consonance with God's purposes or working against them -- can be passed down from generation to generation and preserve cultural and religious norms. With newfound authority, the principles of Wisdom can sometimes be so stressed as to be overwhelming to common sense.
Thankfully, sometimes Wisdom gives way to common sense and averts the dangers of absolute social control. This surrender is exemplified within the Hebrew scriptures themselves, most prominently in the books of Job and Ecclesiastes (although Ps. 73 is a simpler, shorter example).
let's look at the book of Job. It challenges the norm, which regularly attempts to iron out the contradictions between real-life experience and theological systems. The character Job experiences a major conflict between tht two. However, to his credit, he refuses to surrender either, and demands instead that God reconcile the two, basically, by making an appearance and presenting an apology (i.e. a defense, not admission of guilt). Divine beings, unfortunately, live a life of their own and make decisions that are inscrutable to us humans down below. Consequently, Job's request is impossible. God, however, has plans of his own. Instead of defending his governance of the universe, God instead makes Job realize that the divine majesty transcends the small moral categories of Proverbs. God is not interested in the questions that torment humanity, but rather he wants people who will tremble before him.
In summary, it is evident that, at the level of Wisdom literature, God is said to promise to run a universe that is consistent and reliable as he is. However, as far as his people can tell, the system fails sometimes fails to make sense of personal experience and leaves them confused as to what can really be trusted. The only final solution is the realization that God is great and humans are as a mist, and that gap can provide sufficient reason to those with faith to, at the very least, keep on at life, believing that the reliability of their Creator does not turn on whether or not they understand the way he chooses to govern the world.