Keep your w2 income and health care as long as you can.  

Cleveland is often known for its famous sports teams and continues to develop the riverfront area between the stadiums.Cleveland’s job market continues to grow with a sizable push from the health care industry as well as large companies such as Cliffs Natural Resources, Forest City Enterprises, Sherwin-Williams, KeyCorp, and NACCO Industries.

There's be no Fed, and we'd still be on the gold standard, you'd shop for your own health care and it would be competitive, and tuition would costs would be within reach; on and on where the free market has been manipulated because "we" demanded it and then we blame capitalism when it doesn't work out the way "we" wished it did. 

The female patients and visitors ALL had better nails than this hard working nurse and they all had had more expensive cell phones.Knowing I was taking care of them, while paying for their manicures (and health care) with my taxes, really contributed to my burn out.   

I'm also a high earning W2 health care professional and a 401k is a great way to lower taxable income. 

Many in the medical field though are frustrated with pay systems and healthcare reimbursements.. its not all wine and roses :)  but the folks I know in medicine like you say do quite well and are intelligent enough to invest wisely. 

There is no harm in trying out but you should never lose your job if brings your good income and build Social security and healthcare benefits for you.At this internet age, you can work from home and do multitasking, you shouldn't be losing your job for new venture.

I have the added cushion of having government healthcare (I'm a Navy vet), so I'm covered there, though my wife is not.

Healthcare Finance, new real estate investor

How are you handling health care?