So yea, those circle arrow rotating things, that splits you off to 2 diff direction to fight 2 pests. Any suggestion on how to get diff group to diff path? Timing or mostly based on luck?

It's apparently completely luck based. Re-do the map after you complete it if you did not get all things.

Most you can do is stuff as many girls as you can along that route. Two or three girls per route with branches if you want to cover the entire map.