Compare Tom and George (Wilson).
This can be done with a Venn Diagram. Draw two big circles on the page. One side will be marked "Tom". The other side will be marked "George". The two circles must overlap. On Tom's side, you write Tom's characteristics. What does he look like? How does he behave? What is his personality like? On George's side, you write George's characteristics. In the overlapping middle, you write the shared characteristics. The main purpose of this Venn Diagram is to help you brainstorm and organize ideas for your essay.
What attributes does each possess?
This should be included in the Venn Diagram.
Would George have been able to transcend his class circumstances to rise above the ashes?
After you make your Venn Diagram, you take a look at George's characteristics and imagine him as a real person. If you were George, then would you fulfill the "American Dream"? The American Dream is tied with the Protestant work ethic, in which a person is believed to work hard and succeed based on merit. That success can be stereotypically characterized as a wife, 2.5 kids, a house with a white picket fence, and a dog. The American Dream is captured in this song.
What is class structure like in America today?
For this part, you probably want to look at the American social class. Wikipedia may not be the best resource for this, but it does collect a wealth of credible references for your research. If you need help on finding information on social class in America and how people classify social class in America, then you may consult a librarian at your local library (assuming that you are in the United States of America, which has a very robust public library system).
Can the poorest of the working poor leave their circumstances surrounding their situation? Why or why not?
After you read information about social class in America, you have to imagine yourself as a member of the working poor. You should also consider the book's portrayal of social class in America. If you were poor, then could you achieve the American Dream regardless of condition? If you believe yes, then explain why. If you believe no, then explain why not. "Why or why not" is another way to say "explain your choice".
Give specific data as it relates to class structures today - you must research this question and provide statistics to support your analysis.
You will probably have to do a lot of research on various concepts - American Dream, social class in America, social class classification in America, working poor in America. Race in terms of skin color also plays a big role in social class in America (slavery, racial segregation, race riots, race discrimination, race tensions, race-based gangs and terrorist groups, etc). However, in the story, I think the two characters are white men (or at least, in the movie version, they are portrayed by white men), so that's not going to matter much. Social class can be classified by percentage in America. You may have heard "the top 1%" in the America mass media. The author is likely referring to the top 1% of the American social class system, which controls whatever percentage of the American wealth.
Hopefully, my explanations will help you get started on your research.