Did mine 2 years ago
I needed to replace the cutlass bearing on my oday 30 when I bought her 2 years ago. I looked at various possibilities. First I tied to remove the strut from inside-Impossible-Glassed in over the bolts. Then I looked at removing the rudder> Again A big job on the hard. So I uncoupled the shaft from the engine,And removed the prop.Then I took a sawsall and cut a halfmoon out of the glass of the rudder in line with the shaft , being carefull not to cut too deep.(The shaft will not clear the rudder otherwise). I was then able to remove the shaft straight back, bearly making it past the rudder . I cut the old cutlass bearing out with a sawsall and replaced same with new and then reversed the process. After the new bearing and shaft was installed I used a micro ballon/mix to fill the void.(See the West System at any Marine store).Once this had cured I faired it out and put a layer of gellcoat on and you would never know I made a cut. It has been 2 years with out any sign of a problem. I understand that some yards have a bearing puller if you want to just replace the cutlass bearing, but I could not find one locally.hope this helps.