Seeing how Jimmy was supposed to be 15, he should have been an incoming 10th grader. So one would think that a sequel would (if set at Bullworth) bump him up to a Junior, with all new missions and places to access that he didn't get to first time around. Maybe access to some buildings that weren't accessed first time....The Autoshop, The Observatory (which could maybe be fixed up), the third floor of the school. Maybe the return of the Hobo from outer space, as an intelligent being.
Might have been nice to have a real snow or a real snowstorm to try to do missions in. For being set in New England, there is damn little snow during Chapter 3. What about piles of leaves to rake in the fall in Chapter 2 ? Or maybe some real thunderstorms in Chapter 4 ?