I see it that way too, Clayton. I actually attempted to make that very point the other day.
As such I agree with your theoretical framework. What I asked was more of a practical concern. Punishment of crimes, be it prison or restitution, is mostly disincentive. I don’t think most people could ever be happy about the restitution they received for the death of a loved one, the purpose of the punishment is to disincentivize that murder in the first place. And that disincentive would disappear once people get too rich to care about the fines, which we can expect in a undistorted market. Let’s use texting while driving on a private road as an example. Say to drive on a private road you have to agree to the following clause: “If I am caught texting while driving on this road, I agree to pay 1000 Dollars to the owner.” That should keep people from texting, right? But say you are a billionaire, would you care about the fine? You wouldn’t care about lousy 1000 bucks, so you’d just be texting. The whole system of fines loses it’s effect once people become too rich to care about it.