Well mine doesn't collect water on the port side, so the layout must be different on newer Pilot 34s. Mine is a 2003.
But it won't be easy to do. You have to create a depression in the fiberglass to let water collect, place a nylon fitting with a hose barb on the bottom, run a hose to the transom and put a fitting on the transom to connect to. The fiberglass work will be the toughest as you can only access it from the top. But good fiberglass guys can do miracles, but miracles aren't cheap.