A method of collecting data used in assessing total cost of owning enterprise computing systems is provided. The method includes distributing, to an enterprise computing system, an electronic data file that identifies, for use by a data extraction tool, predefined data source fields within the enterprising computing system and that relate to costs included in a predefined cost model that defines costs to be included in an analysis of a total cost of owning an enterprise computing system. The method also includes receiving, from the enterprise computing system, cost information aggregated using data extracted using the distributed data file, wherein the cost information is structured in conformity with the predefined cost model. The method further includes using the received cost information to formulate benchmark total cost of ownership cost information that is structured in conformity with the predefined cost model.