The present invention includes: a step for generating feature amount vectors of a first rolling bearing, which are formed of feature amounts of vibration data on the first rolling bearing; a step for performing machine-learning for the feature amount vectors of the first rolling bearing and damage sizes of the first rolling bearing to generate a first regression model for estimating the damage sizes from the feature amounts; a step for generating a feature amount vector of a second rolling bearing, which is formed of a feature amount of vibration data on the second rolling bearing; and a step for estimating, by using the first regression model, a damage size of the second rolling bearing from the feature amount vector of the second rolling bearing.
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