I have no experience with the boat in question, but when I pulled the shaft on my 1988 O’Day 322, I removed my strut bearing (I have a tool for that), unbolted the transmission flange and removed the shaft coupling, and finally removed the shaft log. Removing the strut bearing and the shaft log gave me a little of play in the shaft and just enough side-to-side okay that I could slide the shaft past the rudder. It was tight, and I took paint off the rudder. Getting the shaft in was even harder…having to not only try and get the shaft slid in, but also having to push the shaft into the hole in the hull. I had to flex the shaft a bit to get it in, until the end cleared the rudder.
Greg