My 1994 H26 rudder is quite heavy - does not float. You need to loosen the wing nut that clamps the rudder in position and the up haul line will pull it to about horizontal, but not further. To get it the rest of the way I either use a boat hook to pull it toward me, or a spare line made into a lasso and carefully tossed over the rudder and then tightened. I normally keep the rudder up and lassoed, and cleated off, when at the dock. Either of these requires some minor technique and practice, but the previous owner said it wasn't possible without taking a step down the swim ladder with the ladder down, and getting your foot wet while grabbing the rudder by hand. So I guess I'm happy I don't get wet and I think either of these methods are much safer than stepping aft and off the transom.
Also, with the wing nut loose especially, it requires some care for the rudder up haul (is looped and also serves as down haul) line to not get out of position with the guides - wedged in between the rudder and rudder side retaining plates - which will bind the rudder tightly in some undesired position. If stuck, you need to loosen the wing nut even more to free and properly align the line again. Not loosening the wing nut too much, and also maintaining a slight tension on the line while hauling up the rudder by lasso or boathook, seem to solve the problem of the line wanting to bind.
It took some practice but now is usually pretty straightforward. If anyone has a better solution, I'd love to hear it discussed.