Kyle, you can ollie off the wake when doing a wake 2 wake. You don't have to though. Some people say you need to edge all the way thru the wake. I think they're just riding way back and need the extra drive to cross the wake. I always let off my edge right at the wake and do a half-way ollie, not really kicking the tail too hard - just kind of half-way. Just punch the tail down and lift the legs, front first, and then push the front back down like a skateboard. This is especially important on smaller wakes or in the flats to get good pop. Notice how my front foot is near the tip of the board to push it back down level for the landing...