How do we perform conceptual modeling? What are common modeling difficulties? Which tool support assists modelers in what respect? The paper at hand reports an update of the design and development of a modeling observatory integrated with a modeling tool in support of studying conceptual modeling. The modeling observatory implements a multi-modal observation approach including tracking modeler-tool interactions, recording verbal data from modelers while modeling and surveying modelers about their modeling processes. A configurable observation setup provides support for conducting studies into individual modeling processes and analyses of modeling processes at the individual and aggregate level. We report on the current state of prototype development, a proof of concept in two exploratory studies and an outlook on future work.