The US obsession with literality in recent times is very sui generis (and even then you have a lot of people criticizing it for not taking further, e.g. the fish is a tangible asset SCOTUS case). In Portugal, the law specifies how it should be interpreted (1966 civil code, art. 9)

1. Interpretation should not be limited to the letter of the law but should reconstruct the legislative intent from the texts, taking into account the unity of the legal system, the circumstances in which the law was drafted, and the specific conditions of the time when it is applied.

2. However, the interpreter cannot consider a legislative intent that does not have at least a minimal verbal correspondence in the letter of the law, even if it is imperfectly expressed.

3. In determining the meaning and scope of the law, the interpreter will presume that the legislator has adopted the most appropriate solutions and has expressed their intent in suitable terms.

It doesn't help make the meaning of the text more determinate, but it may shift where the battle is fought.

I agree in some sense, but spirit of the law also creates very uneven playground and leaves a lot of questions. The way I see the problem, it takes way too long for us to legislate anything. By the time something passes different levels of approval, whoever has any skin in the game might figure out a way around it.

That happens a lot with finding loopholes in housing related legislations. If there is a proposal that would hurt investors, they lobby against it for a while, buying time to figure out an alternative method, and by the time it passes, they don’t really care because they’ve circumvented it anyways.

I see why it would also suck if we fast tracked most of the legislations though.

US Tax law is the only place where I can think of that the spirit is the most important part of the law. There isn't much of a hard and fast definition of a home based business, but if the vibe is "this is a hobby and I'm using the business only to claim deductions, not turn a profit someday" you can be in violation.

Most laws have preambles and records of the debates to help with their intent.

The theory of strict construction is a protection in our legal system. Otherwise you'll end up with a system similar to the insurance you're complaining about - generalized rules, you won't know the outcome going into it, and they can find ways to make the rules for the desired outcome. (This stuff happens in the legal system today, it would just get immensely worse)

I agree that it’s very frustrating, but law is a language game between opposing parties. There is always going to be willful misinterpretation, because, well, sometimes people want incompatible things. If you add a spirit of the law TLDR, you’ll need a spirit of the spirit of the law, and so on.

If the letter doesn't follow the spirit then fix the letter, don't add on more crust.

https://xkcd.com/927/

As I've gotten older, I've found that I've lost a lot of belief in the law at all. Despite being rather clever, we are still primates who live in primate societies. Some of us are greedy psychopaths and some of us are generous empaths. If you put the greedy psychopaths in power, it will have deleterious effects on society regardless of whatever scribbles you have on paper.