Today digital art is important as both a hobby and a career, taking many forms from images to animations to 3D models. Creating unique digital art requires feature-rich art software, which can take dozens of hours to learn even the basics of, deterring many aspiring artists. This thesis begins by exploring art software difficulty by examining peoples’ learning struggles with feature-rich 3D modeling software through a survey, identifying themes of struggle and comparing them to education and software design theories. Turning its attention from people to software, this thesis then analyzes existing art software and video game tutorials to create a taxonomy of features that art software and games usually have - comparing features of often successful modern video game tutorials with features of often failing art software tutorials. Finally the best tutorial strategies for feature-rich art software are identified by analyzing how previously seen strategies alleviate the learning struggles of artists.