"Find The Raincoat" is shorthand, in our family, for gaming the system. The source is an anecdote about a business trip, long ago, where the traveler was sent away on such short notice that he arrived at his destination with nothing to keep the rain from ruining his suit. He bought a raincoat, and included it on his expense report. The company declined to reimburse him for it. He then revised his expense report, removing the raincoat but modifying other items, and resubmitted it with the exact same total. And a note reading "find the raincoat".
That traveler had to game the expense-report system to get reimbursed for an expense that the company forced him to incur. My car's automatic transmission forces me to plan ahead and manipulate it to get acceleration when I need it (this is why expensive cars have powertrains described as "responsive"). When people take short cuts across lawns (see The Parsley, a blog about landscape architecture), they're doing the same thing.
Gaming the system is an indication that the system doesn't do what its users want it to do. The designers' vision (or budget) was inadequate. On the other hand, some systems are built without any concrete expectations of how they'll be used. The fractally expanding world of social media is a prominent example. In many social media platforms, gaming the system is the point; the technology has just been thrown out there. It is almost literally a game to explore all the possibilities.
At this week's blogger meetup, Bill Callahan pointed out that a few years ago, the discussion at these meetups was almost all about the content of the blogs--current events, politics--and hardly at all about the mechanics. The expansion of technology has brought a whole new generation of curious users with it. I'm guessing that this is in addition to the political bloggers, but I'm too new to the scene to say.
So there is a difference between a system that's the only tool available for an unavoidable task (like sidewalks or your car's transmission) and a system made available for people to do--or choose not to do--new things. Between rigidity (you might say obligation) and flexibility or choice. Where is the raincoat in this analogy? Probably in the first category.