This work analyzes the feasibility of using procedural generation to create challenges in a video game based on the player's choices, such as weapon choice, and to compare that approach to one based on the player's skill as well as one based on generating content randomly. Few games have attempted to procedurally generate ways for the player to progress through the game, by generating challenges that keep the player learning new ways to use the existing mechanics. This work attempts to expand upon those concepts by three different ways of tailoring content to the player. We built a video game that generates content procedurally using the 3 aforementioned approaches and had several users test 3 different versions of the game, one for each approach. Our results suggest that, in this particular implementation, players preferred playing the random approach to the approaches with content procedurally generated, which leads us to believe that more work needs to be done to better understand how player adaptation needs to be implemented to improve play experience.