By Paul F.P. Pogue, Angie's List The cold of winter and the rains of spring both take their toll on your roof. Itâs a good idea to get your roof inspected at least once every few years. Experts say the most ideal time is during either spring or fall. This allows a professional to assess the problems caused by the previous season and prepare for the upcoming changes in weather. Regular inspections also allow your contractor to catch small problems before they become big problems. And where roofing is concerned, big problems can become very expensive big problems if not caught before they start leaking.