Difficulty is one of the key drivers of player engagement and it is often one of the aspects that designers tweak most to optimise the player experience; operationalising it is, therefore, a crucial task for game development studios. A common practice consists of creating metrics out of data collected by player interactions with the content; however, this allows for estimation only after the content is released and does not consider the characteristics of potential future players. In this article, we present a number of potential solutions for the estimation of difficulty under such conditions, and we showcase the results of a comparative study intended to understand which method and which types of data perform better in different scenarios. The results reveal that models trained on a combination of cohort statistics and simulated data produce the most accurate estimations of difficulty in all scenarios. Furthermore, among these models, artificial neural networks show the most consistent results.