Just checked this post again Chris.
Check this photo of Byerly coming in toeside for body and handle position.
Compliments of P.Chandler...
This isn't a great example cause he really isn't that hard on his toes (due to the thigh high wake) and has the rope out with his arm dragging cause he's about to grab the board, but it's one of the only pics I have on this computer of a toeside approach.
I have both hands on almost all the way into the wake and am a little more over the toes. The mistake most people make is coming off the toes before getting to the wake and you balance will be toward your heels. Try to stay on your toes all the way up and through the wake keeping the board under you as you cross the wake. Lay it down and go for it just keep the rope in tight so you have some play once you leave the wake.