Reading through the thread some, I could see him being able to remotely access a terminal he's already had access to.
What if he had to install a backdoor into the security of the system he planned to slice first? A virus or something? Then he could access it with a datapad. Maybe he doesn't even have to install it himself... It gets plugged in by the sneaky droid and he's in from the ship.
Would that make sense? It still requires some legwork to be done, but it keeps him at the relatively safe distance that wireless grants,