It would seem economy insurance with high deductibles is now about $1000 per month, compared to about $300 per month four years ago. Unless you net less than $30k per year, in which case it will still be about $300 per month. One simply shops around for what is available in your State, and shop every year when it is time for renewal.
The way I made the split from employee to self employed, was to chart out and cover with designated savings, all our family expenses for one school year. We did not wish to relocate 4 kids during the school year. Plan B was to find employment elsewhere and relocate our family after the school year was up, if this did not work out. By the time we got to the end of the school year, I had earned and saved enough to cover the NEXT school year. Having the funds available without the worry of generating business was the only way to sleep at night.
That was many years ago, and now I have greater fear of growing complacent.