In various embodiments, a bootstrapping training subsystem performs sampling operation(s) on a training database that includes subjective scores to generate resampled dataset. For each resampled dataset, the bootstrapping training subsystem performs machine learning operation(s) to generate a different bootstrap perceptual quality model. The bootstrapping training subsystem then uses the bootstrap perceptual quality models to quantify the accuracy of a perceptual quality score generated by a baseline perceptual quality model for a portion of encoded video content. Advantageously, relative to prior art solutions in which the accuracy of a perceptual quality score is unknown, the bootstrap perceptual quality models enable developers and software applications to draw more valid conclusions and/or more reliably optimize encoding operations based on the perceptual quality score.