> The very mechanical understanding of a contract means that we cannot tell the difference between a transaction that abides by the rules and one that exploits a bug in the system, respecting the letter of the law but not its spirit. This is really the key issue, which is difficult to change. I can't think of many important systems where we wouldn't expect human intervention if something goes wrong.
I'm not sure having humans in the pipeline ameliorates this issue as much as you think it does. Take the existing legal system in the US – laws are interpreted by courts/judges/etc, who AFAICT generally choose to interpret laws by their letter rather than their spirit. As an example, you can look at the recent Kyle Rittenhouse trial with regards to whether or not it was legal for Rittenhouse to be carrying his firear…
The US legal system is based on English Common Law, where precedent and interpretation by a judge have force of law. This is in contrast with Civil Law where the law must be executed as written and judges have very little room for interpretation. Note that in North America, both Quebec and to an extent Louisiana continue to follow the Napoleonic code.