[derekp7]

Absolutes are often bad (i.e., zero tolerance). And many regulations are absolutes. It isn't enough to comply with the law as written, you have to comply with the strictest interpretation that a judge may come up with. And that may not be enough, because some court may be even more creative in their interpretation.

Also often times business like regulation, as it forces all their competitors to play on the same playing field. Which may be easy enough for established players, but is a difficult mote to cross for smaller up-and-coming organizations (regulatory capture).

Then there is the the frequent enough occurrence of conflicting regulations. For example, the EPA may require that an oil change shop store used oil above ground (underground storage can have undetected leaks). But the fire department requires below ground storage (above ground is a fire hazard). So which regulation do you violate? The one that fines you less, and the fine is a cost of doing business.

[A4ET8a8uTh0]

Yes. Without careful stewardship, the compliance becomes a very weird dance, where regulators might focus on things that actually undermine the original intent of the law. For different example, lets look at the BSA front in US banking system, where SARs as a system was developed primarily to assist LEOs, but due to overzealous enforcement by various regulators, banks effectively threw their hands in the air and collectively said "Fine, we will report everything." ( look up defensive SAR filing if you are curious about the details). And now we are in a weird situation where LEOs have to sometimes say things like "If you file it, make it stand out and tell us why it matters so that we can use it"(paraphrased).

Unintended consequences of good intentions.