In collaboration with world-renowned jugglers and mathematicians, this article investigates the dynamics, control theory, and mathematics underlying the computer modeling of a specific class of juggling patterns known as siteswaps. It examines the relative difficulty of juggling various siteswaps, proposing a framework for classification based on simulations using inferred performer-specific probabilistic parameters. In addition, the article develops and features novel visualisation utilities, such as polar state diagram representations.