A portable item reporting device may be attached to a portable item, embedded within the portable item, or integrated into the portable item. The device is configured for sustained collocation with the portable item, and includes a sensor or sensors to locally monitor portable item environmental factors. The reporting device provides self-monitoring services for its associated portable item. The device can identify usage(s) or behavior(s), environmental context(s), or operational parameter(s) of the portable item. The reporting device is a generalized monitoring device which can be configured for use with and is adaptable to a wide variety of different portable items, for different users with varying intended uses for the portable item. The reporting device can be dynamically configured and adapted to identify and provide alerts for a wide variety of displaced conditions, that is, for problem conditions which are unique for a particular portable item, a particular user, and/or particular context of usage. The device may be configurable for different removable types of sensors.