About fifteen minutes into the picture, Mark and Gordon are seen traveling up Mass. Ave. in Cambridge, adjacent to the Harvard campus, and suddenly, they're not on Mass. Ave. anymore, they're on Quincy St., a couple blocks away. Then, just as suddenly, they're right back on Mass Ave., again proceeding through Harvard Square, just as they were before.
After Mark is arrested, he is beaten up by baseball players while in jail. This takes place shortly before Thanksgiving and baseball season of any kind would be over by then.
Mark is planning to attend Harvard Law School for three years, but a plaque showing the scholarship shows that it is awarded to a different student each year. It looks like Mark is ultimately going to have to work for most of his money no matter what happens in the film.
Even if Mark had updated his driver's license before his arrest for speeding, that new license would have to be a fake because his fraud would have been exposed at the DMV for trying to get it with his altered appearance.