Angus:
Anyone deliberately dropping a 500lb bomb in an inhabited city is ipso facto deliberately targeting civilians.
"Collateral damage" is nothing more than a nice, sanitized, insipid, feel-good PR way of covering up that fact a prime example of what Orwell was on about when he said: "The great enemy of clear language is insincerity. When there is a gap between one's real and one's declared aims, one turns, as it were, instinctively to long words and exhausted idioms, like a cuttlefish squirting out ink."
It's declared aim will always be to destroy a "terrorist leader" or "military infrastructure" or "supply routes" or "terrorist assets", but the real aim of a 500lb bomb is to indiscriminately destroy, kill or maim everything and everyone in it's blast radius. A 500lb bomb has an 50% kill rate at a radius of 60m, and an accuracy of about 9m from target. If you put that blast radius in a city, you will kill civilians; ergo by deliberately using a 500lb bomb, you are deliberately killing civilians. And all the feel-good PR in the world won't change that.