re: Been experimenting with "health insurance" for a year and a half

In May of 2005 I moved in with my then-girlfriend, who later became my wife. She was living in one/half of a double in Chalmette. She knew the landlord personally. The double was not in a flood zone. However, I was nervous since it is in south Louisiana, so after moving in, I bought $40K of contents-only flood insurance. Everyone, including girlfriend and landlord, told me it was pissing money away. 4 months and 11 feet of water later, that check saved my (and my future wife) rear end.

My thought on health insurance for someone in your situation (age, status, etc) is that you don't buy it for the everyday cold. You buy it for big, huge, major, accident-type things. A decent trauma event could easily run up 100K in medical bills (after negotiating it down). It would take you almost 28 years to be able to self-fund that reserve, using 300 a month.

Even if you don't want the Obamacare premium assistance, look around (not just BCBS) for a very high deductible insurance plan. Something with at least a $5,000 individual deductible. Pay it, and take the difference between 300 and the premium and put it into a health savings account. It's a tax deductible contribution (as is your premium since you are self employed, assuming you show a taxable profit).

My personal opinion is that the additional "reward" is not worth the significantly more additional "risk" you are taking. You can make a couple of very simple decisions that won't change much of the reward but will significantly reduce your risk.

Again... you can be insanely healthy, and still get hit by an uninsured motorist while crossing the street.