I'm not sure I can articulate my first reaction to this discussion, I may be over my head but I'll give it a try. I know that it's important to have a grasp of the technical aspects of things like response curves, dynamic ranges, etc. But one of the most important factors contributing to the success of a capture (to me anyway) is a real sense for the light. That little tingle of recognition that comes when looking at a print in which the subtlety of the afternoon sun (for example) contributes something to an image that is just as important as the subject itself.
I often find myself being trapped by the exercise of trying to make every value in an image fall perfectly into place only to lose the subtlety of the light that may have attracted me to the scene in the first place. Maybe only the person taking the photo who was actually there at the time of the shot is in a position to judge if the light feels true.
For instance, in Mojo's example, I can't tell if it's morning or evening, Fall, Summer, hot or cold. Which makes it hard to comment on what needs to change or how to change it. Maybe what I'm trying to say is that perfect fidelity in terms of dynamic range can take away from certain images as much as it adds. Some interpretation and rule bending can enhance the impact of a photo.
In the example, the strong light raking across the ground between the truck and the fat lady looks weak and my mind wants it to be stronger. There are ways to make that happen, but they would likely move things into "improper" ranges. But doing so might actually enhance the quirky juxtaposition of the dog and the fat lady poster.
[whew, that was hard.... thanks for your patience]