I can hire a team of lawyers and finance people to set up a complex system of subsidiaries so that my company only realizes profit in a specific way in a specific jurisdiction to avoid taxes, and as long as we've all followed the letter of the law, there doesn't seem to be any problem with the 'spirit of the law'. In fact, entire companies of accountants, lawyers and business consultants exist solely to help other companies follow the letter of the law while avoiding the spirit of it.
What makes it so that laws regarding anything "tech" get to be written and interpreted so vaguely and widely (from warrant canaries to copyright issues etc) when rules for everything from finance to oil spills are narrowly defined and interpreted?
I think that's actually a perverse case of survivor bias. You don't really get to be a significant oil or finance company without intimately knowing how to work with / play the regulatory system, so the ones you see still standing are the ones who really know how to capture the regulators. If you have an oil company worth $5 billion, you have figured out how to make regulators work for you.
Luckily, in the US at least, it's possible for a few nerds to build a company (say, Dropbox) that's as financially valuable as some long-established government schmoozers but has never thought about regulatory issues. So the "young" tech companies like Microsoft, Apple, Google, Facebook, etc. are less capable lobbyists on average.
I can hire a team of lawyers and finance people to set up a complex system of subsidiaries so that my company only realizes profit in a specific way in a specific jurisdiction to avoid taxes, and as long as we've all followed the letter of the law, there doesn't seem to be any problem with the 'spirit of the law'. In fact, entire companies of accountants, lawyers and business consultants exist solely to help other companies follow the letter of the law while avoiding the spirit of it.
What makes it so that laws regarding anything "tech" get to be written and interpreted so vaguely and widely (from warrant canaries to copyright issues etc) when rules for everything from finance to oil spills are narrowly defined and interpreted?