Travelcrazy -- the amount of miles you have on American during the year does not come into play. It is strictly based on FF status and time of check-in. You could be Plat with 10,000 miles and I could be Plat with 60,000 and if you check-in first, you list first. You are correct that a Exec Play would bump me down on the list.
I think AA people have a huge amount of leeway in providing upgrades. For the most part, they follow the ordering rules. However, I have been given a 1st class seat after I was bumped from a flight (the new flight was 20 minutes later, so I know I was not "high" on the list).
--Jim