Well, I practise in the area of tax, so I do see where you're coming from. Just look at the TFSA when it came out.... Revenue Canada right now is constantly giving out rulings because people are trying to circumvent the rules and trying to do certain things.
I do appreciate what you're saying. However, maybe the answer is that the system is so complex and so convoluted that taxpayers don't know really how they should file. Maybe that's why there are so many grey areas: because people just cannot understand the legislation. It's too complex. As for the new laws right now, if they were simpler and easier to follow, perhaps people wouldn't go into all this great detail to circumvent the law.