On our H23.5, we have a large-opening D-shackle on the trailing edge of the rudder, about at the midpoint. The hole is sealed with epoxy to prevent saturation of the core. We use the uphaul to get the rudder to horizontal, then snag the shackle with a boat hook. The 0.000001 kts loss of boat speed due to drag doesn't bother me!
I have two rail cleats spread wide on the aft rail and a line with a snap shackle at the midpoint. I attach the snap shackle to the rudder shackle & center the rudder between the cleats. It keeps the rudder from dropping down and helps decrease waggle. I also have a PCV pipe, 2", I think (maybe 1.5") & T on top. The tiller goes into the T and the pipe goes into the cockpit table leg holder. This also decreases waggle. I use this often for brief moments to keep the course steady when initially motoring out while tending to other tasks.
When we're anchored or at the slip, we will push the tiller to starboard and tie it off. Obviously, you can't move the table to the cockpit if the tiller's in the way. Depending on how long we anchor -- and how much we are dancing due to wind or current -- we might leave the rudder down. Lifting the rudder seems to help decrease any dancing on the rode, which is a bit of a problem with our high freeboard.
If I'm leaving her at the slip and snotty weather is expected, I'll use a line to put a clove hitch on the tiller and affix either end to the aft cleats. I push the knot as far forward as I can and it holds the tiller very snuggly.