This study explores the opportunities created by subjecting a system of interacting fast-acting parameterizations to long-term single-column model evaluation against multiple independent measurements at a permanent meteorological site. It is argued that constraining the system at multiple key points facilitates the tracing and identification of compensating errors between individual parametric components. The extended time range of the evaluation helps to enhance the statistical significance and representativeness of the single-column model result, which facilitates the attribution of model behavior as diagnosed in a general circulation model to its subgrid parameterizations. At the same time, the high model transparency and computational efficiency typical of single-column modeling is preserved. The method is illustrated by investigating the impact of a model change in the Regional Atmospheric Climate Model (RACMO) on the representation of the coupled boundary layer–soil system at the Cabauw meteorological site in the Netherlands. A set of 12 relevant variables is defined that covers all involved processes, including cloud structure and amplitude, radiative transfer, the surface energy budget, and the thermodynamic state of the soil and various heights of the lower atmosphere. These variables are either routinely measured at the Cabauw site or are obtained from continuous large-eddy simulation at that site. This 12-point check proves effective in revealing the existence of a compensating error between cloud structure and radiative transfer, residing in the cloud overlap assumption. In this exercise, the application of conditional sampling proves a valuable tool in establishing which cloud regime exhibits the biggest impact.