Abstract: The disclosed technology concerns methods, apparatus, and systems for using telemetry data from a large number of remote computing devices to address complex problems otherwise prone to subjective inaccuracies. Particular embodiments disclosed herein involve classifying the difficulty of solving (or completing) an objective presented by a certain item of digital content. For instance, certain example embodiments involve collecting telemetry data from hundreds or thousands of users engaging with a respective content item, and, based at least in part on that telemetry data, assigning a difficulty classification to the content item.