The routing I suggested could get you over 35K + an additional 100% bonus if you are plan it right. See: mileage display. That could yield as much as 3 or more free round trips within North America or at least one ticket to Europe or even Asia.

What class of travel will oyu be flying? If economy, you want to join AAdvantage with a Canadian address (has certain advantages such as getting 70-100% miles for your class of travel on CX, BA and QF).

What you want to do is look up the American Airlines forum for the topic: elite "challenge". You want to start your challenge on the 1st or 16th of the month you start flying but BEFORE you start flying. You might want to consider going for Platinum.

Also avoid flying IB as you won't get any miles with them.