What you are asking is a tall order. Look here
http://airlinepilotcentral.com/airli.../american.html for current info.
I'll refine your questions a bit to make my point. You are basically asking the following.
What is American doing in say 8-9 years including information on future contracts/pay scales?
In this future world, how hard would it be to get a 767 line in Chicago?
In this future world with unknown future pay, what will the real estate (apartment) market be around KORD (O'Hare)?
Concentrate on finishing high school and getting into a reputable university/college. I'll let others advise you on ERAU and your chosen field of study.
I understand your curiosity but come back to earth. Long range plans are good but keep them general in nature and don't forget how important today is in this future world you dream about. Close this forum for a few years and go study for your algebra test.