only you, the user knows! motor insulation design life is 30 years but :
how critical is the motor? are there backup/spares available incase of unexpected failure? for example: sump pump motors might get meggered once every 3 - 5 years whereas the exact same motor used in a nuclear safety related application or Navy warship might get meggered twice a year. What is most important I think is the TREND. So you establish a base line megger value of the new motor or new winding if after a rewind. A brand new winding should be meggered before installation. Then after one year or two (next outage) repeat the megger and continue at this pace until you start noticing a downward trend, you would want to SCHDULE a refurbishment. After all, the only reason to perform preventive maintenance such as megger testing is to prevent that operational failure which could cost jobs; scrap the motor; and always seems to happen right before a holiday!