Metal-carbon bond functionalization leading to C-O bond formation is a promising component reaction that can ultimately form the basis for production of methanol from natural gas. Two primary pathways have been considered: (1) an organometallic Baeyer-Villiger (OMBV) pathway, and (2) a two-step, redox oxy-insertion. A series of first-row transition metal methyl complexes was modeled for these two pathways to elucidate any trend therein. Several important conclusions can be derived from this research. First, the OMBV mechanism for wry-insertion is only preferred over the redox pathway in those cases when the metal methyl's d" electron count is such that the latter mechanism would render a chemically infeasible formal oxidation state for an oxo-methyl intermediate. Second, moving toward the so-called oxo wall effectively ameliorates one thermodynamic "sink" (i.e., oxo-Me intermediate) in the redox pathway. However, both oxy-insertion mechanisms suffer from the same feature that would thwart catalysis; i.e., the [M-II]-methoxide product is in a thermodynamic sink relative to the [M-II]-methyl reactant. Third, future experiments in hydrocarbon partial oxidation catalysis should focus on effecting oxy-insertion with the weakest oxidants and in establishing the linkage between thermodynamic and kinetic oxygen-atom transfer potentials of oxidants.