General Overview:

This year's tournament is formatted on a Compass Draw Tournament with a playoff added to the end. What is a Compass Draw?

A compass draw is a tennis tournament draw that is divided up into 8 brackets, each bracket representing a point on a compass (i.e., North, South, North-East, etc.). When a player loses a match, he or she simply moves into a new bracket. This is shown in Figure 1 below.
All players start in the middle column of the large draw shown at the center of Figure 1.
In round 1, winning players move into the East bracket and losing players move into the West bracket.
In round 2, winning players in the East bracket stay in the East bracket, while losing players in the East bracket move into the North bracket. Similarly, winning players in the West bracket stay in the West bracket, while losing players in the West bracket move into the South bracket.
This process continues in rounds 3 and 4 where players can also be moved into the Northeast, Northwest, Southeast, Southwest or Quarterfinal playoff brackets.
If you lose, your matches get easier. If you win, your matches get more difficult. Ultimately, players will gravitate toward a regional bracket with players of similar abilities.
Winning your regional bracket earns you both a regional title, and a playoff birth!
The region you win determines where you'll be seeded in the playoffs.
Once in the playoffs -- It's single elimination to the championship!