Here, we synthesize a library of TCNs and TCNDs that incorporates a broad functional group scope, including imides, diesters, and monoesters. We assess their structures and properties, investigate their ROMP behavior using G3, and compare the results to analogous exo-NB derivatives. We identify trends in the relative propagation rates across these monomers, showing that while their HOMO energies are good predictors of reactivity, readily computed steric parameters (e.g., volume, solvent accessible surface area (SASA), and Sterimol B5) offer overall better structure-reactivity correlations across all exo-NB, TCN, and TCND monomer classes.