I agree that simpler rules are generally harder to work around.
_However_, I notice that argument is almost always made to claim that governments shouldn't try to change behavior in line with the preferences of their electorate. Tax laws have loopholes, regulations have loopholes and push jobs and industries overseas, etc. The logical end point seems to be that democratic processes are doomed to be ineffective and we should just trust everything to the invisible hand of the market.
What if the real problem is that the mindset that improving policy is so hard that governments shouldn't even try, itself dooms us to bad policies?
What if 20 years ago we had all said, "making complex rules to identify and block spam emails is too hard; there will always be some way for the spammers to get through. So let's not waste resources on it."