Health insurance costs may become a bigger headache than a shrinking portfolio for boomers trying to retire young. How to stay covered. Back when mark turret sky was an entrepreneur, building a business empire that sold pork rinds, cotton candy and beef sticks in bulk, he seldom worried about insurance. His only health hiccups were high cholesterol and acid reflux - common problems for a guy his age. So he had no qualms about coverage when he decided to take the plunge and retire early, at age 55.
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