An analyte measurement system includes a processor connected to a biosensor providing analyte data corresponding to an analyte level of a fluid sample. A user interface provides a menu of functions to a user and successively receives a plurality of menu choices, which the processor records. A storage device holds data defining a first action criterion. The processor compares the menu choices to the first action criterion. When the stored menu choices satisfy the first action criterion, the processor can automatically add a first additional function to the menu of functions, or can automatically presents a reward token via the user interface. The system can also include a housing holding the user interface, the storage device, and the processor. Methods are also disclosed.