Some points to consider:
I. Question 1): By what mechanism might sulfuric acid serve as a catalyst to promote nitration of benzene?
2. What do you know about the relative reactivity of benzene rings that bear electron withdrawing (EW) vs. electron donating (ED) substituents toward electrophiles (like NO2+)? Then, when a ring contains both EW and ED substituents, which type of substituent is likely to win out in the competition to direct attack by an incoming electrophile?
3. Question 2) implies that the first nitration step places NO2 into the 3- (or 6-) position of veratrole, leaving the 4- (or 5-) position free to incorporate NO2 in the second nitration step. Can you explain why you believe that substitution by the first NO2 group prefers the 3- (rather than 4-) position in veratrole?