Examples of systems and methods for controlling or monitoring a fleet of human-propelled, wheeled carts and cart retrievers are described. The carts can be shopping carts at a retail facility, and the cart retrievers can be used to collect and return the shopping carts from a parking lot near the facility to a cart collection area. The carts or cart retrievers can monitor various status or usage parameters (such as retriever battery charge, cart collection trip speed, cart collection path or duration, etc.) and transmit the parameters to a central control unit. The central control unit can analyze and process the status or usage parameters. The system can provide a user interface for access to the status or usage parameters of the cart and cart retriever fleet.