I've been long confused by the nature of health insurance in just about every country. America (as should be obvious) is particularly dysfunctional, but shouldn't this essentially be a financial product protecting against sudden uncontrolled or unwanted medical expenses? You have a risk – that of developing a costly health concern – and yet the product available for purchase... is required to... pay for yearly physicals?

Contraception pills, whatever you may think of them, are not a sudden unexpected but unbearable expense. If insurance covers it, they'll just charge you $10 more bucks to give you an $8 product for "free". It doesn't make sense as a financial product at all, and certainly doesn't mitigate any financial risk! Is there some risk that the price of yearly physicals will change substantially faster than my insurance premiums?

The best way I've heard people imagine American health insurance is as a healthcare prepayment service, except it makes even less sense than that! Health savings accounts are prepayment services, really. The current system is so complicated, and has so actively thwarted all simple ways to be useful it basically just sucks.

The horrifying thing is that, even with the massive subsidies (not just Medicare and Medicaid, but employer tax subsidies for health insurance), there seems to be a growing trend of healthcare providers operating completely outside the insurance system. This should shock the world deep into our bones – given Obamacare restrictions, a local doctor's office provides physicals that have to compete with free. Their other appointments are up against other surprisingly subsidized options. And it seems like they do compete!

Of course, there used to be high-deductible plans which almost fit my aesthetic for purchasing things that make sense, but now they have the mandate to cover all of the routine and cheap medical expenses, either don't do the job of covering extremely low-probability expenses well, or they cost quite a bit – typically both. Right now, bizarrely, given my current state lets you buy insurance back-dating to the beginning of the month, and there is protection against pricing based on illnesses you have at the time you signed up, the correct financial product might be not being insured at all. If you hit the unexpected expense, get insurance then, and maybe cancel afterwards?

I'll be real with you, my money isn't where my mouth is on that one. And you ought to triple check you local laws and policies before you make any unusual decisions. But this is honestly the best analysis I have. Get insured, if only so you don't have to worry about it. But we've messed up the system so much that bulk exit may be the best option, for people thinking critically about finance and risk.