Brian,
Great questions...made me wake up more than my coffee....
I started from your image so at this point, I would say that you need to set the neutral and go from there.
In general I set the neutral, highlight and shadow at the beginning and make my adjustments from there. Finding a neutral sometimes requires you to think out of the box...Remember Black and White can be neutral. I found a spot on the tree by setting a neutral and shopping around with it. If you have not watched this video yet you might want to....
www.curvemeister.com/video/greg/honest_abe.swfYou know, on my monitor the image did not look flat and there certainly is room for differences there. I would say that you need to make it look good for your work flow and settings. If you can see full detail in the "significant" shadows then go with your settings. Same with the highlights.
In the second example, I wanted the blues in the middle of the desgn to come up a bit. So using the mouse I found the portion of Cyan curve where the blue parts of the design live. I then put a "bump" into the Cyan curve there. As for "how did I know" It was my goals for the image.
Having targets for each image is one of the toughest ideas to get across to people but one that ends up making the most difference in the images. For me, I start by looking objectively at the image. What problems do I see, how do I think I can "fix" them, what compromises along the way will I have to make to get there..Sometimes I even write them down. Mostly, I speak them out loud. Drives my wife and kids nuts...
K in CMYK is what makes the shadows Black and adds depth to the colors that are there. Remember K represents black ink. You can make shadows with CMY, you just need more of each color. For the print press more ink is a huge problem..makes the end product muddy looking. The commercial solution is the K channel which gives the shadows depth, reduces the amount of CMY needed for overall saturation and is a handy tool for us to use to give the image snap...BTW it is also one of the best "Mask" making channels...when we get there... K can be a sledge hammer sometimes...or if you go slow a feather duster...
Greg