Re: anyone changed a cutlass bearing in a shamrock
When I worked on Shamrocks about 15 years ago they were all pressed in. I used a 2 piece coupler that fit the shaft and strut and pressed them out with hydraulics. I now have a simular set-up and I removed my strut..... took it to a shop to have the bearing pressed in, since my boat is a little wide to be towing. Don't know how you feel about rebedding your strut, but I now feel comfortable about it being secure and watertight.
Otherwise I would take her to a shop that works on them. They can be difficult for the DIY.
Good Luck!