Most valuable sites for a raider to strike, most critical sites for a conqueror to strike (including communication satellites or towers or wires, railroads, bridges, etc); likely landing zones, how exposed they are and how far they are from potential target sites; who has authority over the garrison, and whether any corporations or nobles have their own forces onworld; any colonies or outposts elsewhere in the star system; how frequently do ships come in, and what kind of ships; what's the current tension-level of the indigs, are there any potential flashpoints; who's in charge of the world, of the garrison, of military supplies or necessary civilian supplies, are there any opposition leaders...
Which friendly civilian organizations (eg, Blue Star cult) are most likely to get in the way; major festivals, most popular form of recreation...
Big empty expanses that nobody onworld cares about; jungles, badlands, or nuclear/chemical wastelands which are hard to search; any old, dead cities I can pick through for useful tech...
What levers do I have to get local powers to do what I want, what levers do they have to get me to do what they want...