We develop a unified many-body theory of two-photon dark-state laser cooling, the workhorse for preparing trapped ions close to their motional quantum ground state. For ions with a Λ level structure, driven by Raman lasers, we identify an ion-number-dependent crossover between weak and strong coupling where both the cooling rate and final temperature are simultaneously optimized. We obtain simple analytic results in both extremes: In the weak coupling limit, we show a Lorentzian spin-absorption spectrum determines the cooling rate and final occupation of the motional state, which are both independent of the number of ions. We also highlight the benefit of including an additional spin dependent force in this case. In the strong coupling regime, our theory reveals the role of collective dynamics arising from phonon exchange between dark and bright states, allowing us to explain the enhancement of the cooling rate with increasing ion number. Our analytic results agree closely with exact numerical simulations and provide experimentally accessible guidelines for optimizing cooling in large ion crystals, a key step toward scalable, high-fidelity trapped-ion quantum technologies.