If I were a Chicago fan, my worry would be that they won in the regular season by being a maximum-effort team who crashes the boards and flies around the court on defense. It's a lot harder to out-effort teams in the playoffs, when every game matters and teams bring it every night. Most good teams have another gear. Does Chicago?
I'd put Bradley on Rose - while he's played well at the 2, I think he's most useful when he's allowed to harass the ball, and he might be able to create problems for a less-than-healthy Rose. Let Rondo guard Rip until they prove that we can't get away with that - I think he has the length and the tenacity to handle the matchup, and I also think he's an excellent defender off the ball.
The matchup of the series, in my opinion, is KG vs. Noah. KG needs to keep Noah off of the boards. If he can do that, I like our chances. If he can't, we'll need a transcendent, series-long effort from Rondo, Pierce or both to pull this out.