I believe tax loopholes are the nature of higher taxes and the nature of having complex systems. If everything was a little more simple, you wouldn't need the tax loopholes because it wouldn't be that complex. When you use terms like “all or substantially all” in the Income Tax Act, instead of “85%”, or if you use “a reasonable period of time” instead of “36 months”, you open the door to tax loopholes because it's subject to interpretation.
Sometimes there's more clarity now, I think, when it's being legislated, but I'd say that's the exception.