Even some of the worst possible HDHP plans that employees can get have a max out of pocket of $10k/yr (pre-tax) with HSA. So you can say in the worst case OP makes $400k and pays $10k in insurance if he has some major health issues to be addressed. Or maybe just say he makes $390k and has totally free insurance? Even if he’s spending something ridiculous like $50k/yr on a family of eight’s insurance he’s still way better off.