Even through Crook's pessimistic attitude, just like everyone else, he dreams to have is own piece of land or, at least, more freedom than he does on this ranch. But then at the end of the chapter, he changes his mind and says he doesn't want to leave with Candy, George, and Lennie. It is unclear to me why he had a change of heart. Maybe he did not think life would be much better or he did not want to get his hopes up.