Taking up your first observation, I am not sure if the passage sounds Pauline or if we hear it as Pauline because we know Paul. I think, for example, that Augustine read the gospels through the lens of Paul. I am certain Martin Luther and Calvin did so, along with many of their theological descendents. I prefer to try to reverse the order and read Paul in light of the gospel accounts. All of this is only slightly related to the main thrust of your point! I simply could not resist taking the detour.
As to your idea that Jesus, like other spiritual genuiuses, sets out a plan of salvation designed to fail, so that we might be driven or led to surrender the ego, etc.--it parallels a long-standing approach adopted by Christians of various stripes. In the tradition I refer to, the core idea is that both the Commandments and the Sermon on the Mount taken seriously teach us we cannot achieve God's standard of perfection. Ideally, the realization delivers us from pride (i.e. ego gone amuck, ego in charge, etc.)and we turn to God to do the transformative work only God can do.
I tend to adopt the insight, but I think to stop there is a mistake. Once we begin to surrender our ego (or self-righteousness, to use Pauline and Christian language)and depend upon God, we find God has loved us all along. The way to God and life with God has been blocked by our own ego. Freed of "the need to transform ourselves," as you put it, we become free to live into transformation. Changing metaphors, we become free to be as children for whom watching, learning from, and imitating a parent is both natural and a form of healthy play. For us, the Commandments and the Sermon on the Mount become not an end but the ethos of our home, an ethos we take with us into any external environment.
With regard to the second point, I did not mean to imply that God always responds but never in the way we like. Even if that were my position, I'm not sure it would amount to a cop-out, but it surely would be bleak, akin to the old Norse resignation to fate. That is not my position.
Instead, I believe God may grant or deny what we request, in accordance with his wisdom and within "the rules" of the created world. Children ask for many things, all of which they want in a given moment. Being the parent of two, I know this is so, not simply in theory but in practice. That's why the analogy Jesus used speaks so strongly to me. My intentional responses to such requests have included silence, explanation, denial of the request, granting the request, granting a modified version of the request, requiring something of the child he or she did not expect or especially want, explaining why the request was impossible to fulfill, and delay of the request. In each case, though, I responded as I thought best and possible. Let's face it: I had a much larger frame of reference than my child and a greater responsibility as well. I tend to think God plays a similar role with regard to us.
The story of Job can be interpreted along the lines outlined in the preceding paragraph. In that case, both Job and his "friends" have much to learn, though Job is farther along than any of his friends and asks much tougher questions. His questions are so good, they provoke a divine answer! We, of course, are starting to grapple with theodicy. My hunch is the subject would require a book of its own.
A minor point of clarification before I end: The "nonsense" I had in mind is any version of "name it and claim it" theology. This particular passage is one of the classic prooftexts for what I can only regard as theological nonsense.