The main goal was simplicity, you have one controller for general motion of the board, one for additional rotations (very useful when animating tricks), and two controllers for bending the board, which is necessary when you try to animate skating realistically.
The skeleton has "OnGround" custom property, when animating tricks, set this to zero, otherwise the rig will not work properly. Also the ground plane needs to be called "Ground". Such plane is included in .blend
Clean topology, decent amount of detail (~6500 faces without subsurf modifiers), board.png contains texture for the main piece of board, if you want custom deck graphics just edit this image
Made for fun, and for the love of THPS game series :)