I replaced my cutlass last Spring on my 1988 MkII. After haul out, I followed the process In Maine Sails. We got the bearing out using the Strutt Pro with no problem but upon inserting the new bearing, it wrinkled and jammed. My next choice was to remove the shaft. I used the process described in these forums where you slowly force the shaft back using a socket with a smaller diameter than the shaft, and tighten the bolts between the coupler and the flange. After much hard work we got the shaft out and put in a new cutlass. The BIG proplem was that I bent the wings on the flange in forcing the shaft out. The flange is integral to the Hurth transmission. $3000 for a rebuilt trans and new flange and coupler.
What I did was slowly bend the wings of the flange back into .003 tolerance with a crescent wrench and long pipe over the wrench handle. It took many turns of the coupler and flange, but it worked. I cruised to Desolation Sound in June and it's still running fine with little vibration.
I recommend cutting the shaft and replacing the shaft, coupler, packing, and whatever else needs replacing rather than trying to save your old shaft. It could still end up costing me a new transmission.