With respect to taxes and everything that taxes support, the selling point for whatever faction is yelling at the moment, is that #1 is paying less than the other guys who have weaker lobby support. The poor wants the rich to pay more and the rich would love a simple per capita flat tax.

With respect to health insurance, it should be treated similarly to a life Insurance annuity. One can buy-in inexpensively early in the process. The ACA attempts to do this with the mandate. Unfortunately, there is an important complication for health insurance because the payout is a moving target — life insurance has a fixed payout.