In the case of tariff engineering people are using the laws on the books to force regulators to classify products based on what the regulatory authority itself has defined. They are following the rules, just maybe a bit more aggressively and in ways that the regulators had not expected. (hacking) At this point you have to change the rules if you want to prevent these unintended consequences, since you cannot impose a penalty based on language that doesn't exist and cannot selectively apply the law that does exist.
Also judges who interpret the laws ultimately decide what the laws means - possibility even for future similar cases in countries where judges are bound by precedent.
Often the "hacker" solutions go the other way: come up with a thing, then come up with a convoluted non-obvious justification as to why the existing rules don't apply. This doesn't work nearly as well.
For example, the Bitcoin white paper doesn't mention the Howey test. It's not actually engineered to avoid securities law, it's just presumed that anonymity makes it unenforcable or irrelevant. Some of the more recent coins address that, FileCoin is possibly the best example of a "utility token" pretending not to be a security.
On average saying you won’t win and the best advice is to not bother. Although I have seen cases of an average Joe winning. In all cases it took a ton of their time.