I'm not sure how Dick would be brought in on the group, unless they already knew each other somehow and he had a way to notice that she was missing. When she's free, though, she's welcome to case him at school or at GCPD or something. Also, the living conditions are not his fault, he argues - he can't help that it's all he can afford! At least he keeps it clean!
Re: free-running - he probably participated with the club for a while, until Batman showed up and he started entertaining ideas of following in the big guy's footsteps. At that point, he'd have dropped out to a) use those few extra hours for sleep that he was no longer getting at night and b) to hide his style. Yeah, okay, so with the freerunning club he got to show off the acrobatics, which he doesn't do in costume (it's inefficient), but the boy's paranoid. Still, she might have known him before he quit?