Am I missing something, or do those two ideas completely contradict each other?

But those third-party companies would obviously end up with misaligned incentives to serve the sharks in efforts to cheaply buy from unwitting people. Only wealthy people could afford truly trustworthy third-party insurers to help set the price, which again will entrench the wealthy in the ability to preserve their experience at the opportunity cost of other people.

Much like with third party job recruiters, there is just no possible way they won’t be subverted to disingenuously service the wishes of the wealthier party.

In addition to all this, just imagine all the horrible ways that wealthy people could inflict punitive damage on non-wealthy people. You pissed off the wrong person at work? You’re a journalist who wrote an unflattering piece about the politician? So you come home to find some consortium bought out the home you love, no traceable links back to the person who inflicted it on you, and the money involved was a pittance to them but a life-long nest egg for you that you desperately don’t want to have to convert into the purchase of a different home.