The issue here (as with many disruptive tech companies), is the regulatory system. It is illegal in most states to give legal advice if you are not licensed to practice law. If DoNotPay isn't licensed to practice law in California, they can't do this. And unless they have a plan to either get licensed in many states, or somehow change the law, then their business model sucks. It sounds to me that they haven't actually solved the real problem with the $28 million in investment money they took. The particular AI tech will have very little bearing on the company's eventual success or failure.
The real problem isn't the complexity of the arguments in most cases (as your story shows). The real problem is the complexity of the regulatory system. Tesla has to deal with the dealership rules in several states. Fintech companies that handle real money have to deal with financial regulations or else they are smuggling money. Biotech startups have to follow the FDA rules or they are just drug dealers. Legal advice companies will have to deal with the rules too- and their opponents are particularly challenging.
The real problem isn't the complexity of the arguments in most cases (as your story shows). The real problem is the complexity of the regulatory system. Tesla has to deal with the dealership rules in several states. Fintech companies that handle real money have to deal with financial regulations or else they are smuggling money. Biotech startups have to follow the FDA rules or they are just drug dealers. Legal advice companies will have to deal with the rules too- and their opponents are particularly challenging.