Simon and his wife are in good health in their early 60s, but worry about what their health care may cost them in the next few years. They’re too young for Medicare, which kicks in around 65. But paying for private insurance in the gap years between their planned retirement and their 65th birthdays seems like a big financial burden. Must Read Simon plans to retire at 63, when he’ll get $36,000 a year in Social Security benefits. He will also withdraw $14,000 a year from his 401(k), bringing his total re ...