Any good references come to mind? As I���ll build up a list that I can point people to, that hopefully puts them in a better place to solve these more interesting and hopefully rewarding problems.
Since 2003 in one of my courses I've used Craig Larman's Applying UML and Patterns because it has an analysis approach (getting from a semi-complex problem to a working OO solution in iterations, with UML if you want). It's using the Point Of Sale (cash register) problem which is complex yet familiar enough for most people to grasp (no pun intended, GRASP are the patterns he pushes as underlying responsibility-driven principles).
Otherwise, Cay Horstmann's 3rd edition of OO Design and Patterns (Java, but applies to any OO language) should be out soon (I provided feedback on a draft copy last year). It has some good coverage of OO qualities and also uses a realistic problem (Graphics Editing framework, Violet) as the basis of lots of examples.