might get flamed here but, imo i dont think the "ollie" should be used in terms with any other sport than its roots of skateboarding. my reasoning, because the true art of the ollie comes from the pop and lift of the feet. no bindings etc.. just straight up using your feet and the board. ill throw wakeskating in there too.
http://www.youtube.com/watch?v=usSCRZcOPFE&NR=1 http://www.youtube.com/watch?v=W-SeWMszGBs you get the point, i mean i will never win this one but hey its better than arguing about wakesurfing vrs wakeboarding. lol.
and to answer the question so of the biggest ollies i have seen are on wakeboards, you have a couple things in your favor, line tension and force of the water when you push down to almost make it like a small lip. even i got some hops behind the boat.