Hi H.Ness,
Welcome to Laptop GPS World.
Out of the laptop GPS software you listed, Microsoft Streets and Trips 2008 does have street-level coverage, but the 'find' feature has not been enabled for Puerto Rico, yet. You could still use Microsoft Streets and Trips 2008 (and people do use it in Puerto Rico), but you would not be able to search for street addresses. You could still search for 'nearby places' (POIs).
iGuidance 4 does have street-level map data of Puerto Rico, and I recall not that long ago testing if addresses could be searched, and it did work. You can do POI searches.
DeLorme Street Atlas USA 2009 appears to have some coverage when zoomed-out to see the whole island, but when you zoom in closer, roads disappear.
I also now checked Garmin Mobile PC North America, and yes, Puerto Rico street level map data is there, and address search feature is functional. POIs work fine.
ALK CoPilot Laptop 11, just like the above mentioned DeLorme Street Atlas 2009, has no detail map of Puerto Rico.