You really need to get a job that offers health insurance or a spouse with same. You won't be 26 forever. I wish someone had warned me about the true costs of being self-employed when I was your age. Bonus miles/points is a triviality compared to what you stand to lose when your claim is denied or your insurance is canceled just because you passed a birthday. OK, just my two cents. Maybe things will change in 2014 but I wouldn't plan my life around it. The first concern should be, who will actually sell your the health insurance as a self-employed person and DO THEY ACTUALLY PAY CLAIMS?