[jwolgamott]

Step 1: know your medical expenses. Your total cost per year is either a) You are healthy are it is the sum of your premiums or b) You (or a family member) is not and it becomes the sum of premium payments + deductible. In ObamaCare plans, this is basically the OutOfPocketMaximum.

I am firmly in the (b) camp, and see yearly medical expenses as the deductible plus premiums. And so, I pay $1500 a month in health insurance premiums, but have a $1500 deductible and $4000 out of pocket max. Yearly cost: $22,000.

So, depending on your health and tolerance for rick, go for a high deductible cheap premium plan OR a high premium low deductible plan.

As a freelancer, premiums CAN be tax deductible (see a CPA to make sure).