1. A method, carried out on a server system, for incorporating a new place of interest (POI) as a destination, the method comprising: configuring, on the server system, a trip definition including a delay factor indicating an acceptable delay for an arrival at a destination; determining, on the server system, a proposed POI for the trip definition based upon: the trip definition, and a collection of potential proposed POI instances; and issuing, by the server system through a mobile wireless network link to an in-vehicle user device, the proposed POI for presentation to a vehicle occupant; wherein during the determining, the server system processes the collection of potential proposed POI instances, to render the proposed POI, by: establishing POI ratings for individual ones of the collection of potential proposed POI instances, the POI rating for each individual POI of the collection of potential proposed POI instances being based at least in part upon: the delay factor, and an estimate of additional delay associated with the individual POI; and establishing a rank ordering of the individual ones of the collection of potential proposed POI instances based upon the POI ratings; and rendering the proposed POI from the rank ordering of the individual ones of the collection of potential proposed POI instances, wherein POI instances are categorized within the server system by POI type, and where the determining the proposed POI further comprises identifying a particular locality, and establishing a group POI at the locality by selecting a POI type-specific POI instance for each one of a plurality of categories.