This perspective highlights the essential physicochemical factors required for accurate computational modeling of Raman and Resonance Raman signals in complex environments. It highlights the theoretical challenges for obtaining a balanced quantum mechanical description of the molecular target, integration of target-environment interactions into the Hamiltonian, and explicit treatment of strong interactions such as hydrogen bonding. The dynamical sampling of solute–solvent phase space and the incorporation of plasmonic effects for Surface-Enhanced Raman Scattering (SERS) are also addressed. Through selected applications, we illustrate how these factors influence Raman signals and propose a framework to tackle these challenges effectively, advancing the reliability of theoretical Raman spectroscopy in real-world scenarios.