Excerpts from the
Chesapeake Bay Alberg 30 One-Design Associations Mainsheet
If you cut the bearing a little long so that there is ¼" remaining out of the housing, and pull the bearing immediately after hauling while the bearing is still wet between the bearing and the housing and the salt crystals have not yet wedged the bearing in, it will come right out after you release the lock screws, with a channel lock and just a twist (give the bearing a light coat of Teflon grease before installing).
If you cut the bearing long, ensure that it does not interfere with the prop and there is enough space for the cooling/lubricating water to exit the aft side of the bearing.
If your shaft is old, have it measured, as it will wear down over the years and will then start out loose in a new bearing.
Install a grease (zerk) fitting into the body of the stuffing box packing gland. It involves drilling and tapping a 1/8" NPT thread, then install the grease fitting. The ideas is to squirt some grease when laying boat up for long periods to avoid having to close down the packing gland to stop drips.
Normally, there is more cutless wear in the vertical plane than in the horizontal plane.