The main objective is to not crash or cause a crash. Most pilots and even some FAA inspectors will admit that our current body of Federal Aviation Regulations is daunting. Some say it is difficult, if not impossible, to avoid breaking at least some small rule on every flight. They are not the tools of torture that some believe that they have become. The country's preoccupation with legalities and loopholes really has little place in our world of the third dimension.
Most pilots know when they are pushing the envelope of common sense.
The pilots who consistently err in judgment don't pay much attention to the FARs to begin with. The law-abiding ones are usually not guilty of doing the things that the regulations are designed to prevent. Show them the boundaries and most pilots will stay within them. I understand why the regulations have become so cumbersome. The government has lost mightily at the hands of the lawyers and administrators.