My recollection of this arrangement is the lanyard runs aft slightly and directly down to about the mid length of the trailing edge on the board. Naturally, it's a whole lot easier if the boat
is on the hard
and the board dropped over 1/2 way down. A trick I've used in the past is a narrow diameter bolt with the head
cut off a piece of strong sring glued and tied to it (I usually cross drill a hole in the bolt for the string). Duct tape a shop vac to the tube and feed the bolt in from the other end. With luck, you'll hear a clunk when the bolt gets sucked into the shop vac and now you have a "leader" to pull the hoisting lanyard through. A good seal on the sop vac end is fairly important with large yachts as lifting the darn bolt a long way requires a good seal.