Law isn't a simple practice due to the breadth of subjects it covers - but it is very simplified by the human factor. When laws are enforced they are done so after advocacy from a pair of humans and by the judgement of a human for penalty and possibly guilt (in some cases guilt is determined by a pool of jurors).

This means it's very different from programming where we have a dumb machine that is, at it's best ability, able to look at two numbers and tell you which one is bigger. When it comes to software edge cases must be explicit and factors must be encodable - violations must be recognizable by an algorithm and all cases must be covered. Compare that to the law where generally there are a set of guidelines that have slowly evolved over time to cover more and more edge cases - but viewing any law ever written as completely true to the letter would be a mistake - there will always be carve outs and reasonable judgement entering the picture.

I think the main problem with criticizing the creation of more laws is that we don't currently have laws to cover every situation and it's unreasonable to think we ever will - it'd be nice to get rid of some of the stupid ones but I strongly suspect you'll see this town in Italy end up being freed from any obligations since this hereditary claim is pretty bonkers.

Lastly I might point at countries with a long continuous legal history like England which hasn't changed governments violently or due to outside influence in a loooong time. There are a lot of really crazy real estate claims there, sure - but for the day to day stuff, the laws work. The cost of training lawyers might slowly be creeping up[1] but we aren't anywhere near a critical point of being unable to apply laws. I suspect that point will never be reached and we'll just see more and more specialty in legal professions - instead of an advocate in 1820 you can now hire a lawyer specialized in watershed rights. I expect that trend to continue with specialties deepening and growing further apart just like we've seen with development. You couldn't hire an "ops" guy in the 70's - everyone was expected to be well versed in operating system configuration, interaction and most were probably expected to be familiar with design.

So, I don't think this is actually an issue at quite the level you mentioned - but I do think it's one of these slowly creeping growth factors that makes us more vulnerable to societal system collapse.

1. I'd guess really slowly though since even in the US where precedent is a factor most relevant case rulings are probably from before 1870.