I think programmers especially like to view law through the lens of rules they could implement in code. Often they think it can be hacked by violating the spirit of the law while upholding the letter. Law in reality is a much more human thing that takes into account intention on the party of both legislators making the law and the people it is being applied to. Good thing too.

Is this that makes me think attempts to codify law on some blockchain is a doomed exercise most of the time.

This can be a Good Thing, but it depends a lot on the courts not being lazy and taking shortcuts. When I was in front of a judge there was no disagreement as to the material facts of the case, but my guilt and my sentence were decided based on the Court's determination of my intent. The only evidence the court had regarding my intent was my own testimony and the differing hypothesis provided by the police officers I'd had a verbal disagreement with at the scene. Guess whose story they went with.

I think some programmers try to think in the mindset of what laws would/wouldn't be violated if you could somehow fuzz-test a particular aspect of the court system.

I.e., if instead of an individual case, you could generate a million people who all tried to do every potential variation of breaking the law in that way, then what would the curve of the resulting judgements look like?