I replaced my rudder last year, you can do it all yourself if you don't mind crawling around small spaces (a helper is recommended for re-assembly). I ran into a pin that I couldn't remove but otherwise pretty straightforward. If you have the room to drop the rudder, it should only take about an hour or two to get the rudder off and the same to put it all back together. I removed the starboard lazarette liner and gained access through there. I didn't remove the port side lazarette liner because I didn't want to mess with the propane solenoid etc. but would that definitely make the job easier. I was able to reach the port side bolts through the main cockpit locker, going underneath the liner. Put a hydraulic jack underneath the rudder and provide a bit of lift before disassembling the quadrant etc. Then you can just lower the rudder down slowly.
Dig a hole under the rudder or have the boat blocked up high enough - in my case (asphalt), the yard just lifted up the stern of the boat to remove the rudder and replace it, I did all the other work. Here's a picture of what the quadrant looks like - you only need to remove the bolts with the circles (they are on the other side as well):