Pop-Up Points On a Street Map Effect - CAN'T FIGURE IT OUT.

Help - I can't figure out how to do this effect:

Scenario: I've got an image of a city street map in the timeline; I want to designate multiple locations using wingding symbols; I want these symbols to popup (in what appears to be random order) all over the map in about 15 places in the span of approx 2 seconds.

Problem: I thought this could be accomplished with Pro Titler but cascade won't do - I am not sure what will in SV Pro.

Any ideas?