For graduate and upper-class undergraduate students, chemists from the US, Europe, and Japan discuss the challenges in reliable modeling in organometallic chemistry and strategies for addressing those challenges. They explain techniques and survey applications in catalysis, medicine, organic synthesis, actinide chemistry, and other fields. Their topics include a recipe for an organometallic force field, quantitative considerations of steric effects through hybrid quantum mechanics or molecular mechanics methods, titanium chemistry, spin-forbidden reactions in transition metal chemistry, and main group half-sandwich and full-sandwich metallocenes.