Hopefully, this will get the bearing out :
Originally Published 2014 Cutlass Bearing Removal Every now and then a boats propeller shafting need to be replaced. A replacement can be necessary due to corrosion, bending, wear at the stuffing box, wear a the cutlass bearing or a poorly installed/machined shaft to begin with.
marinehowto.com
After it's in, you may want to take a close look at your shaft alignment. Don't know the age of the boat but I've had the same bearing for 22 years and the shaft still has 0.0000" radial deflection in the cutlass bearing. When the boat was delivered new in 1998, a year later I did an alignment. The initial angular misalignment caused a gap of 0.008" on the 4" transmission coupling flange. I finally whittled the gap down to 0.002". I think this MAY be the reason that the cutlass bearing still remains snug around the shaft to this day.