Very nice look at making the move. I freelance on the side now, but I might look to do this in a couple of years if things go (or don't go) well with my next move.
Health insurance wise, we're you able to get coverage for yourself, or are you participating in a COBRA plan from your previous employer? To be honest, health insurance is probably the one thing that would keep me employed in regular salaried position. The fear of having a medical emergency and it wiping out my savings is a scary and totally realistic possibility.