good question - I have often wondered that myself
Calculating multiple rating adjustements

I don't know, but it doesn't really matter,IMHO. A rating is just a number, don't try to inflate it because you will be disappointed in the future. Just enjoy your games :)

Play the one ur closest to beating. When u beat the 200+ player higher then u that will give u alot more points, but consider this, the lower u r the more u get in points overall but the less high his rating will register once u do beat him, wheres if u beat him after u beat the person closer to ur rating u get less points from the higher player but his rating wont drop as much either so looks good in that respect.
I still say play whoever is closest to being beaten and dont put to much stock in ratings overall....
I am about to beat a player rated 6 points higher than me (in one move). I am also winning a game against somebody rated 209 points higher than me. If I beat the person rated way higher than me it will become the biggest upset of the tournament (which would be cool). Should I wait out the first game and beat the other guy first? Also is there anyway to calculate which order would give more rating points? Or is the system designed for it to be the same :p