Trying to make sense of it all can deter even the most systematic of souls. A year ago Barry Wood, a retiree in Plymouth, Mich., was approaching his 65th birthday, making him eligible for Medicare. The former pharmaceuticals manager began compiling a chart, listing and comparing coverage options. But before long, he gave up, he told me recently. Given the dozens of possible insurance plans and the dozens of features within each plan, “it was the most confusing thing I’ve seen in my entire life,” Wood said.