We had cobra through my wife's former job. As others have noted, you can get cobra even if quit on your own. Thankfully, the old job was in Maryland, where sta

We had cobra through my wife's former job. As others have noted, you can get cobra even if quit on your own. Thankfully, the old job was in Maryland, where state law requires insurance companies to offer a continuation policy after cobra expires. It continues as long as you want it and make your payments, and they have offer you a similar policy in the state you move to if you leave Maryland. We pay almost $1000/month for my wife and the kids to be covered. I have no health insurance at all. Because the policy is in my wife's name, it doesn't qualify as a sole proprietor business expense. (If it were in my name, it would count as a business expense as of 2010, even though it's not bought through the business.) Because of preexisting conditions, we can only get private insurance that excludes most of the things likely to go wrong with my wife and kids. We're now in Florida where the state offers an HMO for children in low income families, but you can buy into it at full price if you don't qualify income-wise. Since the pricing is per-child not per-family, and our fourth is due in June, and we don't qualify for the discounts, the HMO isn't a useful option for us right now. (The 'and children' part of our current insurance is a comparatively small expense.)