My top 5 of that list would be
1) Wall of Scams (To reduce and display the amount of fraudulent activity on the site) Scam=Permaban
2) League Upgrade (I have been curious to see the beta version of this)
3) Sportsbetting player vs player (bitmadness.com)
4)Add daily fantasy sports software ( I love fanasty sports like many do here on PO)
5)PO madness Leaderboard (# of Championships, Heads up Finals, and Final 4s)
Bubbler of the Month Rewarded to the player or top 3 players who bubble the most tourneys in a month?