So Troy and I kept ranting after discussing project management tools. Next on the hit list was the un-usefulness of both iCal and Address Book for power users.
Both of these applications are great as universal, OS-level components for storing and managing calendaring and contact information respectively. But, the built-in functionality just doesn't cut it beyond basic usage.
The conversation went something like this "Wouldn't it be great if there was software that leveraged the integration and pervasiveness of these two tools, but had more power user features?"
And I think this is the key. If you can work with standards (which, after all, is what we're talking about, with the added benefit of integration and support at the OS level) but add some special sauce on top -- whether it be UI, extended features, or something else that makes the underlying standard more useful -- you've got a winner.
Troy promptly ran off and found OD4Contact ("It's like iTunes but for your contacts" is the slogan) which seems to be doing that in the contact space. It's going in my "testing" pile for a 30-day trial.