“Will I run out of money before I die?” George Gagliardi gets that question all the time from clients. A certified financial planner in Lexington, Mass., Gagliardi rarely dishes out a simple answer. Instead, he explores creative solutions to preserve retirees’ funds. Individuals in their 50s and 60s often expect Gagliardi to recommend long-term-care insurance. They may assume it’s a prudent way to protect assets if their health declines and they rack up steep bills for an assisted-living...