1" holesaw to cut the hole out, brush some activated GRP resin to seal the exposed ply of the transom, when dry, apply some sikaflex (or silicone will probably do the job ok) around the cut edge of the hole and shove it in there, twisting to & fro to give a good seal in the sikaflex/silicone. A couple of pilot holes for the two A4 csk screws which secure it in place.
Check the thickness of your planing pad to decide how high up from the base of the pad to drill the hole.