I recently picked up a copy of an older book entitled, "Pitfalls of OO Development by Bruce Webster. It covers a lot of down in the trenches type issues such as object oozing (you gotta love that name), conceptual pitfalls, political pitfalls, analysis and design, proper base class creation as well as more higher level architectural issues - everything such as supposedly basic documentation issues, tools and reuse issues.
Is there any one particular part that stands out? Not really, it just coalesces as a nice book on object oriented development.
The managerial side of me really likes part 3, which covers mid project corrections. Some really basic, but nonetheless, down to earth advice.
Since the book came out awhile ago, you can pick it up on the cheap and is highly recommended.