Whatever you do, don't put a hole in it
Seriously, though, all we do is loosen the nut, drop the swim ladder, push the tiller to starboard and reach down (1 foot on the top step of the ladder) and pull it up with 1 hand under the rudder.
I can't take credit for that one, my wife figured that out one day as I went up to get the truck and trailer. I got back and the rudder was already up and tied in place. I was like, what the... How'd you get that up by yourself. She wouldn't tell, told me to guess...I didn't have a clue. At least someone in the family has some smarts.