> Even if everyone had the same utility function with respect to every single possible good and service
The same good or service having different value to the two parties to a transaction doesn't require them to have different utility functions. It just requires the utility functions to depend on variables that differ between the parties. For example, the utility of a given item of food depends on how much of it you already have (the grocery store has a lot more of it than me, so it's worth less to them).
> we've veered way off topic
I'm not so sure. Health care seems like an area where it should be obvious to everybody that non-monetary costs and benefits are a huge factor that must be taken into account.
"If everything had the same value to everybody, which is what is implied by equating "value" with monetary value, the economy would be completely stagnant and no wealth would ever get created."
That's untrue. Even if everyone had the same utility function with respect to every single possible good and service, (i) wealth would still be created (e.g. by a woodworker transforming a piece of wood into a piece of furniture) and (ii) trade would still take place (because, even in the absence of differing utility functions, there are still productivity gains to be had from specialisation).
Anyway, we've veered way off topic. The comment to which you replied "The expected value of all insurance is negative, and that's intentional" was entirely correct, as long as you don't want to use a definition of 'expected value' that nobody uses.