Removing prop shaft
Ideally dig a hole to allow the rudder to be removed. If this is not possible, as a former Tempest owner for ten years, I have removed the shaft using both of the following two methods:
1) Removal of the rudder. If you are able to raise the back of the boat when in the cradle, by jacking the rear of the cradle, you may be able to get adequate clearance to completely remove it. Its only a 30 minute job. Be carefull of the weight of the rudder though: it's extremely heavy.
2) Removal of the engine, by sliding it forward into the cabin. This job is not as bad as it sounds and should take two reasonably practical people no more than one of two hours. At least with this method, you will easily be able to replace the engine mounts. I had to change my mounts as one had failed (without me realising at first). Be prepared for a shock with the cost: they are not cheap for what they are. I made a wooden platform of the same height as the engine bearers and was able to slide the engine straight out into the cabin. It also gave me the opportunity to clean the engine and compartment, and renew the sound insulation.
It's not necessary to remove the prop shaft if you are merely changing the cutlass bearing. I made a puller which removes the bearing with the shaft in place.(I can send photos). If once the bearing is out and the shaft is disconnected from the engine it can be withdrawn passed the rudder.