What type of Cutlass..
do you have?. If it is a rubber cutlass like the one on my 361 has, all you need to do is remove the prop, take out the two plastic set screws holding the cutlass to the SS cilinder and carefully pull back the cutlass along the shaft.You may need some patience and possibly make a tool to grab unto the bearing lip to pull it. If that fails, you may need to go inside, loosen the dripless seal and slide it towards the engine leaving room to introduce something to push the bearing out. In my case, I was prepared to do all of the above but fortunately I was able to slide it back before it became major surgery. You only need to drop the rudder if you have to remove the shaft, and that is really a last resort treatment.Good luck