[AndyMcConachie]

Every example I see in programming books that say something like, "You should do it this way." Always come with the caveat of, "It depends."

For the hard stuff that you would like to see covered the "It depends" part becomes more important. The correct way of handling the really tough cases you're talking about are extremely circumstancial. Thus, a book discussing them generally wouldn't really work. What would probably work better are examples of these tough design issues that include the actual code and some discussion about why specific design decisions were made.

I like reading code from people who had to make tough trade offs in the real world and hearing in their own words why they made the decisions they did. I loved reading Lion's Commentary on the UNIX OS 6th edition, for example.