I had a discussion with my boss not long ago, he's a tax lawyer with a few decades under his belt. I asked him simply if he thinks he'll keep his job for more decades to come. His answer was quite enlightening, mainly because of how concrete it was: The problem with tax law (which is not the only set of laws, and not contract law either, but perhaps automatable nevertheless) is that it's simply come to the point that it is at right now as a cumulative effort of centuries of work. It works additively and builds structures so complex that the title tax lawyer almost becomes meaningless with so many specialties being required; VAT, corporate and personal income taxes, inheritance and property... Any effort to algorithmically digitise the existing law would fail unless it's able to perfectly replicate it in code. All of the loopholes and exceptions, safeguards and declarations, there's immense inertia ahead.

What he on the other hand thinks has been revolutionary is free access to law, advanced text search tools, and software to make filings and communication significantly easier. That's the boring part that speeds your work up so you can spend more time devising plans to get your clients to pay less in taxes, and construct stronger defences.

There are many low-hanging fruits in this process; I wish these guys the best of luck, but it seems to me that the comparisons drawn (Intuit, Adobe, etc.) are not analogues. Lawyers aren't seeking these tools for it doesn't provide them value, it only takes away billable hours away.

It seems like there could be a lot of value in disentangling the web: repealing the original laws and replacing them with a single law that covers everything in one place. Legal refactoring if you like.

I can only imagine that would be a humungous task. And presumably the existence of case law makes it much harder still.

It would be quite interesting to think about what the legal equivalent of unit tests would look like. Presumably a large collections of sets of circumstances and desired legal outcomes. It seems to me that this might be an interesting output of legislatures in addition to statutes (although whether they would/should be controlled by the legisalture or judiciary is also quite an interesting question, as our existing system seems to rely quite heavily on the judiciary being able reinterpret laws in ways the original legislators most likely didn't intend)

Nevertheless, such efforts cover minimal portions already very clearly defined and debated. As another commenter replied, reforms are rarely undertaken for various reasons. One great issue with tax law is also that whatever code you may write is not necessarily guaranteed to be 'better' (fairness, revenue collected, lack of loopholes and edge cases, completeness, correctness... pick your metric) simply because it's code. That's what I thought too; but no longer.