A system and method operating a customer need-based configuration recommendation management system to enhance configuration selection comprising processor executing machine readable executable code instructions to define a plurality of preset user functional requirement definitions for a configuration of one or more sale items to configure an on-sale custom information handling system available via a web interface, wherein the each of the plurality of preset user functional definitions corresponds to one of a plurality of need-based categories of customers, and a stored plurality of list configurations, each of the plurality of list configurations including a configuration of sale items associated with one of the plurality of preset user functional definitions, wherein each of the sale items have a different sale item type from one another and are identified as being compatible with one another according to compatibility data stored in memory. The system and method provide for a graphical web interface to receive a first user input selecting a first one of the plurality of preset functional requirement definitions for a first corresponding need-based category and a configurator for the first need-based category to present one of the plurality of stored list configurations including a configuration of sale items associated with the first selected functional requirement definition and prompt the user to select for purchase the presented configuration of sale items which updates a plurality of accuracy counter variables assigned to the association between each of the sale items presented and the first selected functional requirement definition.