An operations management server associated with a site location having a plurality of distributed assets therein may store a database(s) including a hierarchy of places within the site location, respective places for the plurality of assets within the site location, and pending work orders for respective assets and respective priority indicators associated therewith, determine a respective place associated with a given asset based upon a work order associated therewith and the database, determine a parent place within the site location within which the place associated with the given asset resides based upon the database, and determine at least one sibling place within the parent place based upon the database. The server may also determine pending work orders for other assets, determine a relative priority of the determined work orders, and communicate the determined work orders to a mobile communications device for completion in order of relative priority.