An electronic shopping system, such as an ecommerce retail website, is constructed and programmed to provide online shoppers with the ability to create and manage multiple configurable item orders contemporaneously within a single customer account. Each item in an item order is associated with a “purchase status” which can, in addition to other discrete adjustments, be toggled between “active” and “inactive” states at or before checkout. Each item order is itself configurable in respect of delivery address, payment source, frequency, and schedule. Orders and settings are saved within the customer's account to be recalled, reviewed, refined (if desired), and executed at checkout.