@allstarsuperman: Oh Nightwing wins all rounds. He is easily the best out of them all, he became batman for a while although Tim drake's prep might make him close to equal i can still see Dick taking this.
The next one is more difficult. For me it comes down to Nightwing and Raphael's team. Ultimately whoever uses prep to their advantage better between Tim and Don will take scenario two, not that Grayson and Raph wouldn't play a factor. Slightly leaning toward RR and Raphael.