What's the problem? Just do a Vickrey auction with your insurer, where you bid how much you're willing to spend to stay alive, and they make a counter-bid. If

What's the problem? Just do a Vickrey auction with your insurer, where you bid how much you're willing to spend to stay alive, and they make a counter-bid. If you win, they spend their bid to keep you alive; if they win, they pay out your bid to your next of kin when you die. A perfectly Pareto-optimal solution of revealed preferences! /s